Module 4.1 Flashcards

(258 cards)

1
Q

Organic Chemicals

A

Covalent molcuelces based ont he element carbon

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2
Q

check sheet for examples of alcohol

A

-lines represent the COVALENT BONDS
-All of these molecules are based ont he element CARBON

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3
Q

KEY

A

carbon atoms have FOUR COVALENT BODNS
hydorgen forms ONE COVALENT BOND
oxygen forms TWO COVALENT BONDS

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4
Q

These moelcules on the sheet have two parts
check star one

A

-Chain of carbon atoms bonded to hydorgen atoms .
-This part of the moelcule is called of the hYDROCARBON CHAIN
-the length of the hydrocarbon chain is dependant on the molecule .

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5
Q

check star two

A

-each moelcule also contains a second part
-the o-h ocygen covalnet onded o the hydrogen alcohol group is what scientists call thisese .

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6
Q

all of these molecules react int he same way but why ?

A

as they all contian an alchol group referred to as the FUNCITONAL GROUP OF ORGAIC MOLECULES .

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7
Q

What is a functional group ?

A

Prt of the moelcule that deretmines how it reacts (alchols all react ina simialr way becuse of their functional groups .

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8
Q

Alcohols are a homologous series , what does this mean ?

A

they have the sae fnctional group but each sucessive meember has an additional -ch2 .

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8
Q

my functional gro pis cll
example of me is cholormethane
wat is me ???

A

CHOLOROALKANESSS
yummyy

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9
Q

family of organic molecules is cALLED hydrocarbons

A

hydrocarbons are covalnet compounds containing only the elements carbon + hydorgen .

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9
Q

check sheet for all the hydrcarbons drawn

A

ETHANE has a SINGLE covalnet bond beween he carbon atoms .
-HYdrcarbons that only have a single covalent bond bewteen carbon atoms are called SATURATED hydrocarbons .

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10
Q

ethene has a double covalnet bond between caebrn toms
ethyne has a triple covalnet bond between carbon toms

A

any hydrocarbon with double / tirple covalne bonds betwen carbon aroms are called UNsatruaed hydrocarbons .

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11
Q

ethane is a memeber of the alknane homolgous series key though

A

-Alakanes have NO FUNCTIONAL GRoup BUT STILLR EFERRED TO AS homoglous series

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12
Q

part one of naming alkanes

A

1.the first paert of each name (aka prefix) tells u the NUMBER OF CARBONA TOMS

TABLE ON SHEET MUSTT LEARN AND KNOW

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13
Q

prefixes can also be used to name alkenes

A

alkenes with 3 carboncatoms
-name of all alkenes end in ENE .
3 carbonaTOMS SO PREFIX IS prop ene . PROPENE

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14
Q

Issue with alkenes with mroe than carbona toms

A

-the double bond cn be in different postions .
-TO nme the molecules we have to show the position of the double bond .
-TO OD THAT WE NUMBER THE carbon atoms .

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15
Q

-look at the shhet

A

-the double bond les betwen carbon 1+2
-in the name , we use the LOWEST OF THE TWO NUMBRTD that the double bodn lies in .

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16
Q

as the double bond lies betwen carbon 1 +2

A

the moelcule i called but 1 nee
check sheet of ranother example

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17
Q

-a carbon chain can me numbered frome ither left or right so wheere do we start ?

A

You choose the ned that to produces the LOWEST POSSIBLE NUMEBRS check sheet for the example .

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18
Q
A
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19
Q

in alkenes

A

we use a number to show the position of the double bonds

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20
Q

example of a branched chain hydrocarbon

A

branched chain hdyrocarbonds have a side chain / branch

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21
Q
  1. of naming
A

start by identifying hte longest ahin of carbon atom
the longest chain is 7 carbn atoms LOOK VERYY CAREFULLY WHERE IT IS .
-alaknes with 7 carbon chians are called heptane

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22
Q
  1. naming
A

look at the number of carbon atoms in sid chain
side chain has one crbon atom check dstar one .
-go back to the table - ONCE CRBON ATOM HAS THE PREFIX METH .
-so we call the side chin with one carbon atom the methyl group .

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3. of naming
State the positon of the methyl group on the main carbon chain . -to do tht we number the carbon atoms . -do this from the left the methyl group IS ON CARBON . this is the right one so the moelcules name is 3METHYL HEPTANE (postion of chain how manyc arbon atoms then LONGEST Carbon chain )
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what if we had two methyl groups on carbon 3 ? check sheet
3,3DIMETHYLHEPTAINE
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check sheet again
3,5 DImethylheptaine
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check example 2
do not be caught out , the longest carbon chain is FIVE CARBON S . -where is the methyl group on cabron 3 3methylpentane
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what if we have two side chains and they are not the same ?
check sheet -idenitfy the lonesgt chins and name sof side chian .
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-the name of the molduelse is based on the LONGEST chain
-Side chains are listed ALPHABETICAL witht he lowest possible numers .
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worked out of example with two side chaons in dif places
-longest chain is 8 = octan e one isde chian = methyl as one carbon another side chain = 2 cabrons ehtyl group POSTIONS = methyl is on carbon3 ETHYL is onc arbon 5 IF U WERE TO NUMBER FROM LEF TTO RIGHT , the lowest numbers woudl nt be produced . -SIDE CHINS ARE LISTED ALPHABETICALLY name is 5ethyl,3methylloctane . E COMES BEFORE M ,
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same rules apply with branched alkenes
-longest carbon chain is five atoms . -double bond is between crbon2 and , so it is based on PENT-2-ENE -Methyl grou pis on carbon 3 os moleeucl eis called 3METHYLPENTANE
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STRUCUTRE of methane
-methane has one cbron tom joined byc oelnt bond to four . so molecular formular is ch4
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molecular formula
the molecular formula ells sus the elemnets in a molecle and then umber of toms o feach elemeent methnae = ch4 .
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emprical forumla
tells us hte ismplest whle number ratio of the the atom sof each element in a compound o fncl one to one ratio so emprical formula is nacl
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whe writing moleuclar forumala of orgnic moelcules always but c before h and then ny other elements are listed alphabeitclaly
...
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one problem with molecular formula
does not give us an information on the strucutre of the moleucle 9how the aotms are bonded to eachother )
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second problem with the moleuclar formula
different compounds can have rs can have the same moleuclr formula
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C2H4 O2
ethanoic acid and methyl methanoate -cant tell from the moleuclar forumla alone which compound e are discussing . emprical forumla c2h6 divide by smallest number HICH IS 2 empricl formula is CH3
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IN EXAM , COULD BE ASKED TO WORKOUT THE EMPRICAL FORMULA USING DATA
a sample of hydrocarbon contains 0.48g of carbon and 0.08 gh of hdyrogen calculate emprical formula STEP ONE - wokout the moles of carbon ahd hydrogen by doing MOL = MASS /MR so mol of carbon is 0.04 and moll of hydorgen is 0.08 DIVIDE BYTHE SMALLEST MOL WHICH IS 0.04 U WILL GEt emprical formula as ch2 .
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empirical formula is used to worko out the moelulcar formual .
we know our ocmpound ofr example has a mr of 28gg1. get hte mr of our empricl formula = 14 divide mr of compound by mr of empricl formula =2 times our empricl formul by 2 = C2H4 menng our compound is ETHENE .
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DISPALED formula of hydorcarbon propane
c3h8 3 carbons and eighth ydorgens .
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key ; displayed formula
shows us the relative position of each atom and all the covalent bonds . -KEY ; displayed formual does not show accurate bond angles .
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however , rather than displayed formula - scientists prefer using structural formula .
structural formula shows us how atoms are arranged but does not show bonds . KEY ; need to show atoms bonded to each carbon atom in turn . CHECK SHEET AND DLOOK AT PENTANE TOO .
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Two different versions of chloropropane
check sheet these are called isomers chlorine is afrer CARBON1 in the strucurl formula -chloirne is after CARBON2 in the strucuturl formula .
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What if we need to show a side chain in the structural formula ?
-methylpropane ch3ch(ch3)ch3 -methyl group of carbon atom with 3 hydorgen atoms . -In the strucural formula , we place the meythl group in BRACKETS -As the methyll group is bonded to carbon 2 , In the strucural formul we put it after C2 .
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alcohol group check sheet
key about the alcohol group is hat the covlent bond runs from the Carbon aatom to the oxygen atom so need to show in the moleucle .
44
what is skeletal formula ?
Skeltal formula is the simplest possible way to show the strucuutre of an organic molecule . -we do NOT show crbon nd hdyrogen toms . -Only atoms we show are FUNCTIONAL GROUPS -Instea we show the ocvalnet bonds between cabron atoms and bond to functionl roups . LOOKA T EXAMPLES ON SHEET .
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FINAL EXAMPLE
Haven't shown the covalent bond between oxygen and hdyrogen in fucntional group as it is not a critical to show the bond in the funcional grous (will say if it is essentail thoghghghg)
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what is is the general formula
the general formula is the simplest algebric formula for a memeber of a homoglous seris
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what is the general formula for alkanes and alkenes
- generral formula for alkanes is cnh2n+2 general formula for lakenes is cnh2n
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workout thecholroalkanes
1. each moleucle has two hdyrogen atoms bdoned to a caron atom . -have one extra hydrogen at the end of each molecule . -each moelcule also contians one atom of chlorine . so genral fromula is CNH2N+1CL This step by step process applies to all .
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general formula for alchols
CNH2N+105 HAVE TO show rthe whole functional group . .
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Check sheet for formula for butane
Butane is an alkane with the molecular formula c4h10
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What other thing had the molecule formula c4h10
Methyl propane Butane and methyl propane ahve the same molecular formula , but different sirry curls formulas . Theses are called STRUCTURAL ISers
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Meaning of structural isomers
Molecules work the same molecular formula and different structural formulas
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Chekc sheet for different structural formulas of pentane and learn them
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Check sheet for different structural isomers of pent-1-ene and learn them
Change rhe poison of the double bond and you get pent2-ene
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Another one
Pent-1-nee move carbon 5 to carbon 2
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Another one 2-methylbutene
Take methyl group on and move methyl group onto carbon 3 , to get 3 methylbut1ene
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Taking pent .2ene
We can move carbon 5 onto carbon 2 giving structure 2 methyl but 2 ene And that is all of them .
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Key : ask nws ask have structural isomers which are called cycloalkanes
Check sheet for cycloalkanes of penitence
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Check sheet for structural isomers of 1-chlrprnjtanr (learnnn)
Some stringers nah be r thoight there was a fifth structure isomer . WITJ THR FIFTH CL ON THE methyl group but that’s jus another wya of smdraeing methul ptopane
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Sometimes , different structural isomers have different functional groups .
Check sheet and lesrn
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What is a functional group isomer
Functional gorip jsomers the molecules have the same molecular formula but different functional groups .
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Chain isomers
They diffeeent in the arrangement kf the hydrocarbon chain . Two examples SHEIN a
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Positional isomers
Have different positions of the functional group . On the hydrocarbon chain , one chlorbitane and 2chlorobutane are examples .
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What re stereoisomers
Stereosisomers are moelcuels with the the same struccutrl formula butatoms are arrnged differently in space .
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Stereoisomers
Stereoisomers are molecules with the same structural formula, but atoms are arranged differently in space
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There are two main types of stereoisomers
Geometric jsomers And optical jsomers
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Chekc the sheet for 1,2 dibromowrhanw
KEY: single covalent bonds are fully rotational . AKA THE covalent bond between the two carbon atoms can rotate . All of the diagrams shown for the same molecule all that has been done is in each case is rotate the carbon bond between the carbon mains.
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Showing in sheet 1,2 dibromoethene
Double covalent bonds have very resiteicfwd rotation. A double covalent hind can flex slightly . But cannot rotate like a single covalent bind . This means that this meolcule actually exists in two different forms .
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1,2 dibromowrhwne
These are called geometrical jsomers or 1.2 dibromowrhwne check sheet One is CIS and one is TRANS KEY : cis/ trans jsomers is one of the naming systems for gemeoteixal jsomers . The other one is E/Z
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Any can have cis/ trans jsomers as long as it needs to conditions.
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Condition one
Carbon atoms on the Dublin bond must have attached to 2 different groups. Can see this in the monster drawn before. Both carbon atoms on either side of the double bond is bonded to a bromine atom and a hydrogen atom.
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Condition two
At least one of these groups must be the same, on both carbon atoms on the double bond (in the in the case store, it is actually true for both the hydro and the bromine.)
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Step one on deciding which is which.
Look at the group which is the same on both sides of the double bond. In this case we can choose either hydrogen, atoms or bromine atoms. We’re going to choose the hydrogen atoms in this case.
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Step two of deciding, which is which
– If the two hydrogen atom are on the same side of the molecule, then this is a CISI. – however, if the two hydrogen atoms are opposite the molecule than this a trans is OMR .
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SIS/trans, isomers for BUT – two – ENE
In the case of this, the carbon atoms are on either side of the double bond and are both body to a hydrogen atom and meter group. We are going to stick with the hydrogen again. – In the C.I.S. is more hydrogen atoms are on the same side of the molecule (diagram on left). In trans, isomer and opposite size of the molecule, check the right side.
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Why can’t But1Sbe have any cis trans isomers
What is carbon atoms on either side of the double bond must be to 2 different groups. – at least one of those groups must be the same for both carbons. Looking at but one ehe we can see carbon one bonded two hogging atoms, so but1sbe is not a cis trans isomer .
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What about 1-xhlorobut1eneq
This can have system isomers as a carbons on either sides of double bond is bonded to 2 different groups. (Carbon one is bonded to hydrogen and chlorine atom. Carbon is bonded to a hydrogen atom and eat our group. So here is the C.I.S. Trans isomer for 1-chlorobut1ene, check sheet .
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workout e/z isomer , how do we do it ?
start by looking at the grop ,kw hich is thw same , on the carbon atoms on either side of the double bond . +-In
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How do you workout E/Z isomers ?
Start by looking at the group which is the Same on the carbon atoms on either side of the double bond . In this case we are looking at the hydrogen atom .
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Workout Z isomer
If the group is ok the same side of the molecule then we fall it a Z ISOMER
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If the group is on the opposite soxd of the isomer
We call it the e isomer
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Ada vantage of cis trans jsomers
Check sheet , in this case , the carbon atoms on either side of the double bond are attached to four diffferent groups . -so we cannot name these isomers using cis/trans system .
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BUT , we can use due E/z isomer rule And to do that we use the CIP priority rules (initials from scientists who developed this )
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Step one of using CIP rules
lol at the atoms attached to the carbons on either side of the double bond The element with the greatest atomic number is given the highest priority .
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-On the LHS we have cl and br Chlorine has atomic number 7 and bromine is 35
So on the lhs bromine has higher priority .
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On Hydrogen has ar If nimber onefluroine has nine RHS
So on the right hand side flooring has the higher priority. 
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We assigned the EOD using the higher priority groups. LHS – higher priority groups on the opposite size of the molecule so this is the E isomer .
HS – higher priority groups are on the same side of the molecule, so this is the z isomer .
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Next molecule carbon atoms are on either side of the double bond, have completely different groups.
LHS of the double bond we have a bromine atom and a iodine atom. Bromine has an atomic number of 35 and iodine has an atomic number of 53. So iodine has a higher priority.
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RHS of the double bond – carbon atoms attached to 2 atoms of oxygen. Therefore cannot establish priority based on oxygen. So now we move onto the next atom, if there are different, we can use these to establish priority.
I uncover. The atomic number of hydrogen is one and atomic number of carbonate six. Meaning group containing carbon has a higher priority. LHS – high priority groups are opposite size of the molecule, so it is a R isk ed. . RHS same side , so Aaron
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Determine the e / z isomer of this check sheet
HS – hydro atomic number of bond and chlorine atomic number seven. Chlorine has a higher priority. RHS carbon is one to another carbon so we cannot use this for priority. Then we have carbon and nitrogen. Carbon has an atomic number of six and nitro atomic number seven. Nous containing group has a heartpriority
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General formula of allanes cnh2n+2
Covid bonds all each carbon atom, phones, tetrahedral structure with bond, angles of 109.5°
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The bond angles in alkanes are type of covalent bond, Calls a sigma bond
Aia bond forms when electron orbitals from adjacent orbitals directly overlap . A sigma bond contains a parallel one from each atom, either side of the bond. The par of electrons in the bond directly between the bonding atoms.
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When we look at our Keynes, we can see that carbon atoms. You can’t force a different type of corrode and bod called pi bond .
However, in the case of alkanes, only a sigma bond can be formed.
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Key: sigma bonds are fully rotational.
The covalent bonding in alkanes are also relatively strong. And take a lot of energy to break.
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Alkane is a hydrocarbon. Carbon hydrogen atoms have very similar electronegativity. Many alkanes are essentially non polar molecules.
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Helping to explain the properties of alkanes.
Alkanes are insoluble in water. Because water molecules from hydrogen bonds with each other. 
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Because our kids have no permanent diapers, they can some hydrogen bonds. Therefore, I’ll keens cannot dissolve in water.
Online money or molecules alkanes are generally unreactive. Because of this strong covalent bond within an alkane molecules.
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Certain conditions, arcades will react.
If we look at the boiling point of alkanes, we can see interesting, as the length of the carbon change increases so so temperature. Long-term archives have a higher boiling point as the carbon chain-link increases, we find the arcades at liquid and solids at room temperature.
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You can explain this pattern by looking at the intermolecular forces in alkanes.
Alkanes are non-polar, so the intermolecular forces acting between alkane molecules are included, dipole, dipole interactions.(London (dispersion forces.
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When we boil an alkane, we have to break these intermolecular forces – however, London forces are weak forces and do not take a lot of energy to break. Explaining why shorter chain alkanes have a low boiling points.
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As the length of the carbon shade increases, strength of land forces also increased
There are two reasons for this.
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Number one longer train alkanes have more electrons than shorter chain alkanes (strength of the London forces going go up if the number of electrons enquiries, close bracket.
A second reason – longer train alkanes have a great surface area then short to train alkanes. Meaning that there are many points along the molecule. They can form London forces,. Increasing number of electrons and increasing surface area increases London forces in Longtain arcade, so have a higher boiling point, then shorter chain alkanes
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Branched chain alkanes have a lower boiling points and straight chain alkanes.
As branches, prevent the arcade molecule from getting close together. And London forces are strongest at shortest distances, so in branched chain, alkanes to London forces are reduced.
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Alkanes are extremely useful compounds
Alkanes are used extensively as fuels . Alkanes are used as the starting materials for produce of the whole range organic molecule, including pharmaceutical. You find arcades in crude oil Crude oil is a fossil fuel and formed on the ground from the remains of plants and animals. – Over millions of years, heat and pressure. Convert the chemicals in these remains crude oil.  As we are using crude oil, faster than it’s formed, it’s non-renewable resource.
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What is crude oil?
Cradle is a mix of street chain and Blanchard arcades. Along with other chemical sulphur. – Use these alkanes. You need to separate them using for distillation tied out column. In order to understand fraction station, need to need to learn about the full of arcades.
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Crude oil molecules are attracted to each other by intermolecular forces.
As alkanes are nonpolar – they have the forces. Key: long-term hydrocarbons have a greater serve area for formation of London forces, compared to shorter chain, alkanes. Meaning, it takes more energy to break the London forces in longer chain alkanes, so they have a higher boiling point, then shorter chain arc arc.
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Key: octane alkane – octane boilers at 126°.
If we take liquid octane and heated to 126°, it boils converting to a liquid to a gas. If we take as a gas and we call it below, it’s boiling point it will condensed back to its liquid for (applies to any alkane.)
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Step, one of fractional distillation
Crude oil is heated in the furnace. The temperature of the furnace is hot enough enough to boil a lot of the alkanes in the crude oil, converting them to a gas.
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Step two of fractional distillation
Next, the crude oil, vapours and liquid pass into the fraction column. The column is hotter at the bottom and become progressively cooler going upwards.
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Step three of fractional distillation
No, the crude oil, vapours, make their way up the column. A different levels of the column, we have collecting traits. These trays have bubbles, something which allows vapours to pass upwards.
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Step four fractional distillation
As each alkane moves up the column, at some point, it will read, which is cooler than its boiling point.
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Step five, a fractional distillation
Now the alkane condenses back into a liquid and passes out the column. This alkane with shorter carbon chains have lower boiling input. so we collect them at the top. Long chain arcades have a high boiling point, and therefore collect at the bottom.
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All okay with a very long chain from a thick liquid called bitumen and this is collected from the bottom.
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Not all the alkanes will condense. Very shortened arc, that methane and Ethan are collected at the top as gases.
Key: fraction desolation does not separate each individual arcade. Instead, each fraction contains a number of alkanes with similar boiling points. To separate each individually, we need multiple rounds of fractional distillation.
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Why is the petrol/up the fraction, particularly useful.
The fraction is used to make petrol in vehicles and as of raw material for the chemical industry.
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But what is the problem with the problem with the petrol/NAPA fraction
Crude oil tends to contain a high proportion of long contain hydrocarbons, then solitude. So when we carry the crude oil, we did not produce the last amount of the petrol/the fraction. – In contrast, we produce more of the longer term fractions which are less demand. Because of this, there is an economic benefit to converting long chain, hard carbons disorder, hard carbons. We do this wire process called cracking.
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One benefit of cracking
Cracking converts, long chain, hydrocarbons into short hydrocarbons.
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Second benefit of cracking
As well as producing alkanes, cracking water produces alkanes. Unlike alkanes, which are highly reactive molecules. Alkanes are a major feed stock (warm material) for the chemical industry and are used to make a range of products, including polymers.
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There are several ways to carry a cracking.
The two methods include thermal, cracking and catalytic cracking.
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What is needed for thermal cracking.
Thermal cracking requires both a high temperature and a high-pressure. – Needs to be around 450 to 900° and the pressure is around 70 atm Arcades are converted into short chain ales ales and Al Keynes. – Hydrogen can also be one of the products. The product shown examples of what we could produce. However, I should point out that the specific products depend on the exact conditions.
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The benefit of using thermal cracking
Internal cracking, we make a high percentage of lakebed in produce in the products and as we’ve seen, our canes are very useful molecules due to their high reactivity .
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In the exam you could be also complete. Cracking quiz like this. Given the starting molecules and the sum of the products. 
Remember: the total number of carbon must be the same on both sides of the equator. In different isomers are possible, then that will be taken into account in the question.
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What happens during thermal cracking step one
A Covid and bond between the two carbon atoms splits. To form a molecular molecules. Remember, covalent bond is a pair of electrons.
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What happens during the cracking step two
When the covalent bond splits, both of the intimate in Michael, now fuse, one unpaired electron. Scientist called isn’t molecule like this for free radical. Key, don’t need to know the mechanism for thermal cracking.
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What is needed for catalytic cracking?
Class is a cracking auto, requires a high temperature 450°. However, catalytic Cratic cracking does not require high-pressure. , In fact, the pressure of catalytic cracking is about one to 2 atmospheres.
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What extra thing does catalytic cracking need?
Catalytic crack and use a zealite list. Which contains a mixture of aluminium oxide and silicon dioxide. Zeolite has a large surface are called an effective catalyst.
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What a long okay undergoes catalytic, cracking. The products are often branch chains.
What arcades are special used for petrol as they combust very efficiently. – Catalytic crack also produce cyclic hydrocarbons like benzene. 
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Alkanes are very unreactive, why?
Nonpolar as carbon and hydrogen acids are very similar electronegativity. In later, flashcards, you will see many molecules that react due to the polarity, so because they are non-polar, arcades are not very reactive.
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Open (two) why are alkanes unreactive ?
The bonded arcades are relatively strong. And take a lot of energy. Again, making them unreactive molecules.
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What is one way that alkane can react?
Buy free radicals (a.k.a. as radical)
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What is a free radical?
A free radical is any species with an unpaired electron. Two examples, shown on sheet. We have the rhyming for radical and the meat through radical. You show the unpaired electron as a dot. Key card free radicals are highly reactive species. Even though alkanes are unreactive molecules, they can react with free radicals.
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Free radical reaction between alkanes and halogens.
Reaction between methane and bromine. So the hydrogen atom on the methane molecule, has been substituted with a bromine atom . And this reaction has a free radical, this reacted example of a free radical substitution.
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We can also see if radical substitutes in the reaction between methane and chlorine.
I’m showing you that equation. We also see free radical substitution the reaction between me and chlorine. Showing that equation here.
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Looking at the stages between me and chlorine. These can also apply to any alkane and also chlorine as well as bromine.
There are three stages in this reaction. Initiation Propagation. Termination
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At the start of the reaction, we have a mixture of methane Roman molecule BR2.
First – initiation. We shine UV light onto the reaction mix. The end of the UV light causes single covalent bond between the two bromide atoms to break.
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Part two of initiation
You need to remember that a single covalent bond consist of a power of electrons. – When the bond breaks like this come on one electron now goes to eat breed atom.
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Initiation initiation, part three
Because these now have an unpaired electron, these are bromine free radicals. – When a covalent bond split in this way, scientist called this homolytic fission .
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Initiation part four
I should point out, we only require a few of the broken monitors to form free radicals , in the initiation stage.
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Propagation part one
Romy through radical reacts with a methane molecule. Remember that a Free Radical has an unpaired electron. To make an electron pair, the bromine Free Radical , takes a hygiene atom plus one electron from the methane molecule. In order to illustrate this, electrons are shown in the covalent bond in the methane molecule as a gree green dots. This reaction produces both a hydrogen bromide and a methyl Free Radical
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Propagation, part two
The methyl free radical now reacts with a bromine Melville , producing our end products bromoethene and another bromine free radical .
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What do we see if we look at steps one and two in propagation?
We can see that they form a chain reaction. The bromine Free Radical formed in propagation, step two. Can now go back react with the methane in propagation step one. – This will continue until the final stage which is called termination.
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What happens in termination?
Two free radicals react together form molecule with no unpaired electrons. – This is now a stable molecule and no longer takes place in the reaction.
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There are three possible reactions in termination.
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One possibility
Two bromine, free radicals, can form a bromine molecule.
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Second possibility
To meet all three radicals can form a molecule of ethane.
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Third possibility
Or , Amith are free radical under bromine, free radical conform molecule of Bromoethane
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What is the problem of free radical substitution of alkanes.
We get a whole range of side products. Example bromine free radical, reacts with a molecule of bromoethane then we make dibromoethane . Can get further reactions to form tetrabromoethane .
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What happens in the termination step?
In the termination step, we can make Ethan. This ethane can also react with bromine free radicals. Forming, all molecule step .
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In termination, what happens if we carry out the reaction with longer chain alkanes, for example, pentane.
We could produce a whole range of product molecules.
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Some teachers use curly half hours, describe radicals such as
However, we don’t need to use this.
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Alkane ethane for example
Alkanes or saturated hydrocarbons with a general formula cnh2n+2 All the Covalent bonds in alkane are sigma bonds . Sigma bonds form when electron orbitals directly overlap.
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Key ideas
In alkanes, bond, angles tetrahedral (109.5°.) – Sigma bonds are really rotational.
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Structure of the alkene ethene example
Unsaturated hydrocarbons with general formula cnh2n. Thing to notice is that ethene is a planar molecule . We looked up planar molecules in the topic of structure, bonding . Planar normal molecules of flat, with all the atoms lying on the same plane .
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Remember when working out molecular shapes we treat both single and double bones as bonding regions .
We have three bonding reasons around each carbon atom . These bonding regions repel and move as far apart as possible. – Meaning that bond angles around carbon atoms are around 120°.
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The bonding in ethene is different to ethane due to the double bond .
Just likee ethane , ethene has signs finds between carbon and hydrogen atoms . However, the double bond actually consist of two types of Covalent bondd , When the double bond forms, we form one sigma bond between the carbon atom. At this point, each carbon atom has one electron left in a p orbital. These orbitals lie above, and below the plane of a molecule.
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The two p orbitals over up sideways and form a covalent bond called a pi bond ,
Which is above and below the sigma bond. Key: even though overlap occurs above, and below the sigma bond, we only form one PI bond .
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Key: double bond in our Keane actually consist of both a sigma bond and a PI bond. Which has a major effect on the structure and reactivity of alkenes.
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Difference between sigma bond and PI bond
Unlike sigma bonds, a PI bond can rotate. That’s because any rotation would reduce the overlap of the p orbitals .
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Second difference between the sigma bond and the PI bond
As the PI bond cannot rotate, this means that the structure of an alkane across the double bond is actually locked. Can see this so with 1,2 sicholroethene . As the molecule cannot rotate, the molecule exist as two isomers E and Z isomers. – Al form stereoisomers as double bonds. Can’t rotate.
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Number two, why are are highly reactive
Due to the double bond. – Bond and enthalpy of pie bond is less than a sigma bond. As PI bond is a sideways overlap of the orbitals, where I was in a sigma bond, the orbitals directly overlap. – As the orbitals over up sideways, PI bond is easier to break. – As it takes less energy to break PI bond, it is more likely tobreak in a reaction.
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A double bond consist of two pairs of electrons
So we have a par of electrons in Sigma bond and parallel electrons in PI bond. Because of this – double bonds is a reason of high electron density. This high electron density makes alkenes reactive molecules.
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What does a double bond consits of
a double bond cosnits of sigma bond and a pi bond . -Both of these bodns contain a pair of electrons . so the double bond in alkenes actually consits of four electrons . -this region of high electron densitry determines how alkene reacts .
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There are three hydorgen haldie
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What do we have in a double bond
A double bond consists of A sigma bond and a pi bond . Both of these bonds between the pair of electrons. For the double bond in alkrned Actually consists of four electrons, meaning the double bond is a region of high electricity. This reason of Hi electron density determines how alkrned react . 
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Alkrned react by a process called electrophilic addition.
A Reaction between alkenes and hydrogen halides .
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So there are three are you, Hydrogen halide molecules here.
Key: halogen atoms are more electronegative than hydrogen. This means hydrogen halides molecules. Have a permanent dipole. As you can see, in the hydrogen hate, I don’t want to, the hydrogen atom Has a very positive charge on the halogen atom has a small negative charge.
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How hydrogen halides reacts with Ethan we have to learn this reaction mechanism. Stage one
Hydrogen bromide, Molly to approach is the alkrned The positive hydrogen on the hydrogen bromide is attracted to the high electron density of the double bond, scientists call this and electrophille.
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What is an electrophillr
Is there any positive ion molecule which is attracted to a region of high electron density.
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So, in this case, the positive hydrogen atom in the hydrogen bromide is acting as an electro file
The positive charge on the hydrogen atom, attracts the power of electrons in the pie bond of the alkene. This pair of electrons move Towards the hydrogen atom, and we use a curly arrow to show that power of electrons.
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Key points about the hydrogen halides reaction mechanism
– A covalent bond is a pair of electrons. – When you draw a curry hour, make sure that the arrows starts exactly whether electrons are moving from and ends exactly where they are moving to.
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Stage three
As you can see, covalent bond is not forming towards the hydrogen atom, in the hydrogen bromide. This presents a problem
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What is the problem?
Abhay didn’t atoms can only have one covalent bond. So come at the same time, the pair of electrons in the covalent bond between the hydrogen and bromine now move onto the bromine atom. Shown as a curry Aaron.
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Stage five
When a covalent bond, breaks like this, with both electrons, going to one atom, scientist called is heterolytic fission.
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Stage six
St the end of this stage we now have two products . -we have a positively charged intermediate molecule formed from The alkrne .scientists call this the carbocation intermediate. This contains a positively charged carbon atom.
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Why is this carbon atom positively charged?
Because it has lost its share of the electron pair that What in the pipe on. – We have also found a negatively charged by my own come on. This is a negatively charged because, both of electrons are in the cupboard up come on out on the Brokide ion .
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Key point about this Resction
Number one if we were to look at the whole creation, we can see the hydrobromide has added to the Ethene Examples of an Alexa. .2, the Allen’s in thsi reaction id ethene Which is a symmetrical Monica. Meaning I can only make one for product. However, if we were to carry out a asymmetrical alkene like but 1 ene Then we can make two possible products.
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key ; when we add a hydorgen halide to symmetrical alkenes we form one porduct
showing addition of hydrogenbromide to the symettrical alkneen but2-3n3 . -Showing carbocation inermediate withthe postiive charge on the carbon 2 , Making porduct 2bromoethane .
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Showingresction again , but this time the carbon atom intermediate has a positive charge on. Carbon 3 .
….
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Some might think we make the pros cut 3-brooo butane but why is not the gas e.
We always number from the carbon atom that will produce the lowest possible numbers . -if we number from the right most carbon we can still make 2brokoburaje . SO NEED TO REMEMEBER WE ADD ABHUDIRGEN HAOODE TONSUKMERRICAL WE ONLT MAKE one product .
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Allen’s but1ene . Asymmetrical Alkene .
When an asymmetrical alkene reacts with a hydrogen halide molecule we can actually form two isomers . THIS ADEPENDS ON WHUCH carbon atom has the positive chathe in the carbocation intermediate .
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If the positive charge is on carbon 1 then we make 1bromobursne .
It can have a positive chathe on the carbon 2 We make 2bromobutane . KEY : we dont make equal amounts of these products . We actually make a lot more 2/brokortuane then 2 bromoethane .
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1-bromobitsne is a minor product 2-vrombjtane js a major product . Why
Idea is that a carbocation intermediate is on unstable molecule thag only exists for a short period of time . -the stability of the carbocation depends on how many alkyl groups are bonded to the carbon atom with the positive chathe. .
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What is an alkyl group ?
An alkyl groip is a group containing a carbon and hydrogen atoms . This is shown in red .
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If the positive carbon atom is bonded to one alkyl group
It is called a primary carbocation .
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If the psofige carbocation is bonddd go two alkyl groups
We call this a secondary carbocations .
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KEY : secondary carbocation is more stable than a primary carbocation . As it is kore stable IT EXISTS FOR a
Longer period of time . Therefore is more likely to form a product , explaining why 2brokobutane is a major product and 1bromobutsje is a minor product .
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How to determine major minor product
Look at markowikoffs rule When a Hydrogen halides reacts with an asymmetric alkene, the hydrogen atom of the hydrogen HALD or is more likely to bond to the carbon atom which is attached to the greater number of hydrogen atoms.
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Putting the rule into practise
Going back to but1ene , one can see that carbon 2 is bonded to two hydrogen atoms . Whereas carbon3 is bonded to only 1hydirgen atom . -so in this case , the hydrogen of the hydrogen bromide is more likely to bond with carbon 1 . So 2bromothingy is major product .
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Explain the alkyl groups
As we have seen , secondary carbocations are more stable than primary carbocations . That is because the electrons in the alkyl groups can shift towards the positive charge . -the effect of this is to stabilise the positive chagve . Scientists call this the POSITIVE INDUCED EFFECT .
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In primary carbocations , the positive charge is stabilised by only one alkyl group . Whereas in secondary. Carbocations z, the positive chathe is stabilised by two alkyl groups .
Making it MORE STBALE that primary carbocations .
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2-methyl but1ene - this can form secondary or tertiary carbocaitisb
The tertiary carbocation had 3 alkyl groups bonded tk the positive carbons rom . /making the terraria cabdocaitons even more stable than the secondary carbocations . So the major product would be from the tertiary carbocations .
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Showing reaction between ethene and bromine .
-in this reaction , the halogen molecule adds across the double bond . -another example of electropjile addition hair et as we will see the mechanism is slightly different .
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Why is the mechanism slightly different with halogens ?
As halogen molecules do not have a permanent dipole .
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Stage one for halogens .
-first stage of rs film , bromine molecule approaches the ethene molecule . -bromine Dosent have permanent dipole , however , we double kind of the alkene is a region of higher electron density . -fhis huhh electron density , repels the electron pair of the covalent bond in the hormone molecule . -THIS MEANS BROMINE JSD SN INDUCED DIPOLE
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Stage two of halogens
On stage 2 , the pair dk electrons in the oi bond of the alkrne are attracted the the positive bromine. . So I’m this case , fhe positive bromine is acting as an rlectropjille . -sos from pairs now form a covalent bond in the bromine atom now bread and pairs of electrons love onto the otherr bromine atom . -when a covalent bond breaks like this with both electrons going to the same atom . Scientists call this heteorlyic fission .
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So at the end of stage 2 , we have carbocation intermediate and a bromine ion
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Stage three of halogen
In stage three, the electron lair on the bromide ion , are attracted to the positive cadbocn atom in the carbocation intermediate . /the electron oair Joe forms a covalent bond and we have our final product . Production this case is 1,3 dibromowrhwne .
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Note in stage three
In this reaction , halogen molecule adds across the double bond . -meaning , two halogen atom end up on the adjacanet carbon atom . -we cannot get bjt halogen atoms on on the same carbon atoms .
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One difference between adding a halogen and adding a hydrogen halide
Halogen had induced dipole . Hydrogen js life has permanent dipole
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Second difference adding a halogen and adding a hydrogen halide
Makes only one product with asymmetric alkene . Snakes major and minor product with asumemetricnalkene .
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We can use a halogen to rest for the presecene on unsaturated molecules like alkenes and to do so we us ebromine water
Check if it’s unsaturated add drops of bromine water and gently shake the rest tube . If our substance is usbtwurated then the bromine will add across the double bond and product of reaction will be colourless . If saturated the bromine water can’t react and remain orange .
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Electro hill Iv addition of addition of water to alkenes tk make alcohols
Scientists call this a hydration reaction SHEIN hydration reaction of ethene . - in hydration , the water is in the form of steam and phosphoric acid is used as a catalysts . The temperature js 300 degrees and the pressure ejs about 6p atmospheres
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Hydration of alkenes mechanism stage one
Catalyst for this reaction. Js phosphoric acid . Structure shown Soho’s rich acid has 3 hydrogen atoms each handed to oxygen . /As we have seen , oxygen is a strongly electronegative element . Meaning phosphoric acid is a polar molecule . -oxygen atoms ahve a partial negative chathe and the hydrogen atoms have a partial positive chathe .
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Stage one mechanism (hydration of alkenes)
The pair of electrons I. The pi bond of the ethene of are attracted to one of the positive hydrogen atoms in the phosphoric acid . -in this case , the positive hydrogen atoms act as an relectropjille .
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Stage one of
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Stage one of hydration of alkenes mechanism part two
-now fhe paid dk electrons in the oi bond form a covalent bond to the hydrogen atoms -at the same time , in the covalent bond between the hydrogen and oxygen breaks . -the pair of electrons Joe move complete on to the digger Aron . As we have seen in stage one we have a fabrication intemvolule with a podi r carbon ion and a dihydrogen phosphate ion with a negative oxygen ion .
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Key is that the pjsosphoric acid is a catalyst
Meaning we need to regenerate the phosphoric acid in a layer stage. .
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Stage two of the hydration of alkenes
The carbocations intermediate reacts with a molecule of water. , in the form of steam . Rememeber that the oxygen atoms in the water meolcules have two loke pairs of electrons . -of these lone pairs now form a covalent bond between the oxygen and the positive carbon atom I the carbon stink intel’s . -at the end of season2 , we now have an intermediate molecule containing a positive oxygen atom . this oxygen is positive bevause it’s lone pair of electrons have formed a coal net bond .
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Stage thee of hdtdrstikn kf alkenes
Final stage , involves a hydrogen phosphate ion , we made earlier , the hydrogen ojsoapjge ion forms a cola net bond to snyfrigen in the intermediate disks. -at the same time the covalent bond in the intermolecular now breaks this is herotic fission z And now a pair of elections in the home joenkove coklerly into the thay xx Now we have made our profit ethanol and rheenrated our phosphoric acid catalyst. .
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As we have send the hydration of ethene produce ethanol .
What about asysyemtic sleekness slimempropene xx How do we detmeine what carbon atom will bond to the hydrogen atom of the wnd which to neenejje Hydrogen atoms likeee idek aahruh chekc gmthatbcudeo idk what I’m suaing .
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How alkenes react which hydrogen gas
This reaction is called hdyirgenarikn
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Key points about hydrogenation
Hydrogen Melodie’s add across the double bone . / so when hydrogen jokes srionnwlekensbeucubisbabuhsatueated keolcue we make an alkane which is SAIT aree .
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Reaction for hydrogenation
Also requires a solid catalyst liek nciken . Unlike other reactions in alkenes , hydrogenation does not take place by electro Philip reaction .
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Use of hydrogen work. Js to make margarine
Margarine js made by the hydrogenation of vegetable oils .
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Molecules in the vegetable oils contain fatty acids, and these fatty acids are unsaturated molecules containing one double bond.
Unsaturated fatty acids have one double bond which is why vegetable oil has had no boiling point by hydrogenation. We increase the most important which converts from a liquid into like a solid. However, the conditions are controlled so hydrogenation only passed your cars so early. Sunil is the double ones are hydrogenated to increase the melting point.
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olymers ar used extensively in products
polymers can be divdied into two large categroies -addition -condensation
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Key ; polymers are large molecules
we form polymers by joining togetheer the ends of small identical molecules called monomers . -when we form addition polymers the monomers aare alkanes . -EXAMPLES ethene forming an addition polymer - youneed high temperature and high pressure as well as a CATLAS . then you form poly(ethene )
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polymerism requires high temprature and presure as wella s catalsysts
When alkenes form a polhymer ---> double bond in the alkenes oppen up and join one moenemer to another , -KEY ; polymer is formed sorry maed by using word poly named by the monomer next in brackets . -POLYETHENE is used to make plastic bags and bottles .
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the porduct polymer has no double bonds in the carbon double bond . -yeah
this means that despite being formed from a
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Addition polymer contains a large number of carbon hydrogen and carbon carbon double bonds .
These bonds are both non ppl are are really strong making them Difficult to break . -due to this , addition polymers are unregistered to Molecules . -this lack of rescifocru , means that addition polymers can exist in the environment for a very long time .
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People ask about the ende of polymer molecules
Appears rhat carbon only has three covalent bonds . -need to remember during polymerisation , other molecules are added to up the ends of the polymer chain .
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Instead , scientists foren show the repeating units instead of the whole chain. .
Repeating units show the arrangement of works that are repeated in the polymer chain.
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To identify the repeating unit . We take two adjacent carbon atoms on the main chain
Then we draw two faebon atoms plus the hydrogen atoms above and poolroom . -draw the square brackets around . We then draw the covalent bonds coming from each of the two carbon atoms , extending through the square brackets .
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-we also need to show many repeating units present in the polymer .
The polymer . I am showing has 14 in geh chain for example . So we need to put a number 7(9; example to represent the repeating units .
225
Check the sheet to see how polymers in a reacfion can be represented as
If we know the structure of a polymer . We can workoit thenpolymer Monomer has a double bond but the repeating u tk does not
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Addition polymers are made from alkanes which are produced from crude oil
We saw that addition polymers are very jnreavtive molecules . That js because the carbon hydrogen and carbon carbon double bonds . -are both non polar and relatively strong . This makes the bonds difficult tk break .
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The lack of receiving is one of the reasonably why addition polymers are such useful molecules
Addition polymers to make containers for food and drinks without the polymer reacting with don what
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However , their lack of reactivity is one of the reasons which presents environmental impacts
Additions are non biodegradable . This means , they are not broken down by microorganisms in the environment . Because of this , sdditioknpolymers can pollute the environment receded in . This can be extremely harmful to wildlife -s.g sea birds can be entangled in polymers mehejnlpokojgnfot food . This can be fatal
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Even when addition polymers are used repsosnodmlg , they still involve the use of crude oil which is a non renewable resource
The crude oil needs to be transported and refined which requires energy .
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Because addiifon polymers are used jn such large amounts they can occupy lots of space jnlandfills
As you can see , manufactures and dispose of Addition polymers xan have major effects on the environment
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There ways to reduce the effects
1.firstly , rather than sending waste polymers to landfills they can be combusted , generating energy . 2.hwieger , combusting polymers can release harmful chemicals .
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What is PVC
Polychloroerjsne PVC contains chlorine worms when combusted the gas hydrogen chloride is produced . -hydrogen chloride is corrosive and must be removed from any waste gases before they are release .
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Polymer wars can be sorted into the different poly
Polymers wast can be sorted into different and recycled into new products . By recycling polymers we can reduce use of crude oils and amount of work in landfills . .
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Another type of eexulox Kms Called Feedstocks cycling .
In feedstock replying , waste polymers are converted back to simple hydrocarbons FHESE hydrocarbons can be cracked and conveyed into different polymers . ADVANTAGE- waste polymers do not need sorting . Feedstock trucking allows us to finger one polymer into a different polymers
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Scientists are working on producing new polymers fhag are biodegradable .
They are usually based on billogciak mass plants Benefit of thee elllyners did they naturally break due to the ACGION of kicrograjossm . They seldom Manufacture form oak t materials as renebwske resource
236
HOWBEER
BIodherabslen addition polymers . -science are also working on oil base dooleyenrrs slowing broken down in sunlight called motogrwdwbkenpolyners .
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238
239
Aliphatic hydrocarbon
In which the carbon atoms are joined together in Tibet striaght unbrandhed chains or benched chains
240
Aliphatic hydrocarbon
In which the carbon atoms are joined together in Tibet striaght unbrandhed chains or benched chains
241
Aliciykic hydrocerbons
In which carbon atoms are joined together in a ring structure but are not aromatic
242
Aromatic hydrocarbons
In which there is at least one benzene ring in the sturdier
243
Check page 167 make sure u know all the functional groups
244
How to work out elpeifslnforkulanusijg mass of each element
Chekc page 169
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Why are aromatic hydrocarbons stable ?
They are very stable because the electrons are shared across all the carbon atoms this part of the leaflike is hel take yingogle dijnsjubfrukcislnreacitons and often represented used skeletal formula .
246
How to calculate molecular formula using emotional formula
Check page 169
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What is homolyriv fission
When a coslne thing breaks and each electron goes to a different bonded atom . This generates two highly reactive neutral specials called facials , radicals have one or more unpaired electrons shows as dots Chlorine molecule Yh light .
248
Heeroektic fission what is jt
When a covalent thing breaks and hotje leftrokengontonojenofbthebhojdedbsorksntuisbreiskrsbijbabosituhevgwriojnajdbajuojnheijtnrorkee Broski stuff hrokopsjenjasnandiple
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Check page 186 learn
Table injti
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Check page 190-191