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BI1014 > Organic chemistry > Flashcards

Organic chemistry Flashcards

(60 cards)

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1
Q

what bond angle does carbon have?

A

109.5 and 108.70pm

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2
Q

what happens in carbon hybridization?

A

one of the electrons moves to the 2s orbital moves to the 2pz orbital so there is one electron in each orbital
making the bond angle 109.5
these are all sigma bonds

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3
Q

when forming a C=C double bond, can you draw what this looks like and what is the associated bond angle?

A

120
contains sigma and pi bonds

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4
Q

what happens in sp hybridization? can you draw this?

A

one electron in each 2py 2pz 2sp3 2sp3
bond angle of 180
contains pi bonds and sigma bonds

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5
Q

what are the ways in which carbon can react?

A

oxidation
reduction
substitution
elimination
addition

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6
Q

heterolytic

A

two electrons transferred to a single atom which forms ions

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7
Q

homolytic

A

one electron transferred to each atom which forms radicals

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8
Q

formula for alkanes

A

CnH2n+2

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9
Q

how are side groups for naming listed

A

alphabetically

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10
Q

what are constitutional isomers?

A

same number of atoms but different connectivity

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11
Q

in terms of alkanes, which radicals are the least reactive and least stable to most reactive and most stable

A

primary are least reactive and least stable
tertiary are more reactive and least stable

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12
Q

how are radical stabilised? can you explain this?

A

stabilised by hyperconjugation
when the radical forms, the carbon centre transforms sp3 hybridised to sp2 hybridised
delocalisation of the bonding electrons from carbon next door by overlap with partially filled p orbitals
net stabilising effects (less energy to generate the radicals)

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13
Q

how can alkanes react?

A

combustion
cracking
dehydrogenation
halogenation

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14
Q

cis

A

priority groups on the same side

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15
Q

trans

A

on different sides

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16
Q

what are geometric isomers

A

double bonds and they cannot rotate so are either cis or trans

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17
Q

Z

A

same side
Zusammen

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18
Q

E

A

different sides
entegegen

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19
Q

alkenes in fatty acids

A

cis double bonds result in kinks in the overall structure

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20
Q

what do alkenes act as?

A

nucleophiles
so react strongly with electrophiles

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21
Q

what does a pi bond cause?

A

high electron density in the above and below plane of the molecule

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22
Q

alkene carbocation stability

A

primary carbocation is the least reactive and least stable
tertiary carbocation is the most reactive and most stable

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23
Q

what is Markovnikov’s rule?

A

the formation of a major or minor product
example with an alkene reacting with HBr, the hydrogen will join to from the major product with the carbon with the most hydrogens attached

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24
Q

what is syn and anti addition of alkenes?

A

syn comes in from the top and anti comes in from the bottom, the formation is NOT the same product

this example can be in term of a haloalkene in the addition of water, first the hydrogen, then secondly the OH- is where it makes it syn or anti in the way that it will bind

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25
which of the halogens are most electronegative?
fluorine
26
what are optical isomers
non-superimposable mirror images of each other also known as enantiomers this produces a chiral carbon, stereocentre or asymmetric carbon
27
what is the haloalkane R/S system
identify the chiral carbon assign priority numbers to each group arrange so the lowest priority group is pointing away and then with the remaining groups you can determine based off the number you have given if its going anticlockwise or clockwise clockwise = R anticlockwise - S
28
what does a nucleophile act as?
a base (proton acceptor) donates an electron pair
29
what are the two nucleophilic substitution mechanisms?
Sn1 - unimolecular nucleophilic substitution, so one thing happens at a time Sn2 - Bimolecular nucleophilic substitution, two things happen at once
30
Sn2 mechanisms
only one transition state, so the rate of reaction on both nucleophile and carbon backbone rate second order they maintain enantiomeric purity which may result in a change in R/S at the chiral centre
31
Sn1 mechanisms
high energy cost (the first step or second step) which means that a rate determining step is produced and the reaction may be first order they destroy enantiomeric purity of the sample
32
what happens to the solubility of the alkanol as the chain length increases?
it decreases
33
why are alkanols insoluble in hexane?
because alkanols are polar molecules and cannot dissolve in a non-polar solvent
34
what's an oxonium ion?
contains one too many hydrogens, usually acting as a base
35
are Sn2 and E2 mechanisms the same?
no, Sn2 is substitution with two things happening at once, E2 is elimination in one single step alike in Sn2
36
how do you name ethers?
the shortest hydrocarbon chain becomes the alk-oxy group then followed by the longest alkane chain e.g: methoxy-ethane
37
what are ether properties?
more polar than alkanes but significantly less than alcohols very little chemical activity and commonly used as solvents
38
amines naming
don't forget to say N-methyl-ethanamine
39
carboxylic acid nomenclature
greek letter numbering to reflect the carbons as they step away from the functional group
40
carboxylic acid properties
can be an acceptor or donor but mainly as a donor increasing hydrophobicity of a growing alkyl chain eventually overwhelms the carboxylic acid group arrangement of hydrogen bond donors and acceptors allow for the formation of dimers low melting and boiling points
41
what is more acidic alcohols or carboxylic acids?
carboxylic acids due to the stability of the ion
42
name two factors affecting stability
strength of the bond being broken stability of the resulting ion
43
what does a higher pKa mean?
weaker acid
44
ester hydrolysis
saponification mechanism?
45
uses of esters
soaps grease and the surface, the hydrophobic tail will burrow into the grease and the hydrophilic heads will interact with the washing with water
46
amide formation - cyclisation
the formation of the amide and if the alkyl chain is long enough, because it can freely rotate, this means that a cyclic formation can be produced
47
peptide bonds
only the bonds on either side of the peptide bond can rotate
48
aldehyde and ketone physical properties
stronger dipole than haloalkanes due to the double bond
49
aldehydes and ketones reactivity
ketones don't really oxidise due to CH3 not being a good leaving group
50
tautomerisation
interconversion of two isomers by simultaneous shift of a proton and double bond forms enol (alkene and alcohol)
51
do ketones oxidise
no
52
aldol reaction
53
imine formation
54
transamination
55
cycloalkanes
each carbon is sp3 hybridized rings are non-planar
56
in cycloalkanes, what does the ring prevent?
each carbon isn't free to rotate the functional groups so these structures do not interconvert
57
benzene
all the carbons are sp2 and the double bonds can shift around the ring the ring is planar but does not behave as 3 double bonds delocalised ring above and below carbon ring, making the structure very stable
58
naming the regions on the carbons of benzene
ortho, meta, para
59
how does benzene react?
electrophilic attack - substitution highly attractive to electrophiles no electrophilic addition
60
name the types of electrophilic attacks benzene can undergo
bromination nitration sulfonation friedel-crafts alkylation friedel-crafts acylation

BI1014 (6 decks)

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