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All Mechanisms Flashcards

1
Q

Alkane to haloalkane mechanism name and condition

A

Free radical substitution
Condition = UV light to break halogen halogen bond

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2
Q

Alkane to haloalkane mechanism for cl2 and methane

A

IPT
initiation = Cl2=2cl2.
Propagation 1 = halogen halide formed = CH4 + CL. = C.H3 + HCL
propagation 2 = C.H3 + CL2 = CH3CL + CL.
Termination = any two free radicals combine

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3
Q

Overall equation

A

Check alkane and haloalkane difference eg 2Fs
Add 2F2 and 2HF

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4
Q

What is a free radical?

A

A species with a unpaired electron

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5
Q

Haloalkane to amine mechanism name, reagent and condition

A

Nucleophilic substitution by excess NH3
Excess NH3
Ethanol solvent heat and pressure

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6
Q

Haloalkane to amine mechanism

A

1st NH3 is a nucleophile so attracted to carbon with halogen
Arrow from middle of bond to halogen
NH3 replaces halogen and becomes positive
Arrow from middle to bond with hydrogen to nitrogen
2nd NH3 acts as a base as it’s attracted to hydrogen

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7
Q

Haloalkane to nitrile mechanism name, reagent and condition

A

Nucleophilic substitution
KCN
Water and ethanol solvent

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8
Q

Haloalkane to nitrile mechanism

A

CN with lone pair in carbon attracted to carbon with halogen Arrow
Arrow from middle of bond from carbon and halogen to halogen
CN replaces halogen and molecule has an extra carbon

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9
Q

Nitrile to amine mechanism name, reagent and condition

A

Reduction
H2
Nickel catalyst

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10
Q

What is a nucleophile ?

A

Electron pair donor

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11
Q

What is an electrophile ?

A

Electron pair acceptor

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12
Q

Haloalkane to alkene mechanism name, reagent and condition

A

Elimination
NaOH/KOH
Ethanol Solvent

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13
Q

Haloalkane to alkene mechanism

A

OH acts as a base not a nucleophile
OH with lone pair on oxygen and 1- charge attracted to hydrogen on carbon adjacent to carbon with halogen either side = forms E/Z isomers
Arrow from middle of CH bond to CC bond
Arrow from carbon to halogen
Form H2O

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14
Q

What are stereoisomers?

A

Same structural formula but different arrangement of atoms in space

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15
Q

Why do stereoisomers form ?

A
  1. P orbitals overlap forming carbon double bond therefore no rotation otherwise P orbitals would not overlap
  2. Both carbon atoms in c=c bond bonded to 2 different groups
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16
Q

Does the Z mean that the different groups on the same side or different?

A

Same side

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17
Q

Alkene to haloalkane mechanism name, reagent and condition 1

A

Electrophilic addition
Halogen halide
No conditions

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18
Q

Alkene to haloalkane mechanism

A

H
I
Br
Vertical HBr
Arrow from middle of bond to halogen
Arrow from middle to c=c to hydrogen
Hydrogen attaches to either carbon ( carbocations )
Halogen with lone pair attracted to carbon that is positively charged

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19
Q

Major and minor products

A

( major )Second or third carbocation more stable than primary ( minor )carbocation as more alkyl groups so greater positive inductive effect

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20
Q

Alkene to haloalkane mechanism name, reagent and condition 2

A

Electrophilic addition
Diatomic molecules eg cl2
No condition

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21
Q

Alkene to haloalkane mechanism 2

A

Br+
I
Br -
Vertical Br2
Arrow from middle of bond to halogen ( becomes negative )
Arrow from middle to c=c to hydrogen
Halogen attaches to either carbon ( carbocations )
Halogen with lone pair attracted to carbon that is positively charged

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22
Q

Explain why bromine reacts with a double bond in alkenes?

A

C=C has a high electron density in pi bond
This induces a dipole in Br2 which pushes electrons from centre of bond to furthest bromine
Partially positive bromine attracted to c=c

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23
Q

Alkene to alkyl hydrogen sulphate mechanism name, reagent and condition

A

Electrophilic addition
H2SO4
No conditions

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24
Q

Alkene to alkyl hydrogen sulphate mechanism

A

H
I
OSO3H
Vertical H2SO4
Arrow from middle of bond to OSO3H
Arrow from middle to c=c to OSO3H
Hydrogen attaches to either carbon ( carbocations )
OSO3H with lone pair attracted to carbon that is positively charged

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25
Alkyl hydrogen sulphate to alcohol
H2O H2SO4 catalyst
26
Alkene to alcohol mechanism name, reagent and condition
Direct hydration H2O Concentrated H3PO4 catalyst, high temperature, high pressure
27
Alkene to alcohol mechanism
Arrow from c=c to H+ ion from concentrated catalyst Oxygen with lone pair attracted to carbon with + Oxygen is positive so arrow from hydrogen to oxygen H+ formed at end as catalyst
28
Alcohol to Alkene mechanism name, reagent and condition
Elimination( dehydration) Hot concentrated H3PO4 catalyst
29
Alcohol to alkene mechanism
Lone pair on oxygen attracted to H+ Arrow from middle of bond to positive oxygen Arrow from middle of CH bond to carbon adjacent to one with oxygen Form H2O
30
Haloalkane to alcohol mechanism name, reagent and condition
Nucleophilic substitution NaOH/KOH Aqueous solvent
31
Haloalkane to alcohol mechanism
OH with lone pair attracted to carbon with halogen Arrow from carbon middle to halogen OH replaces halogen
32
Primary alcohol to aldehyde mechanism name, reagent and condition
Oxidation Acidified potassium dichromate , H2SO4 Distillation Uses 1 (O) , produces 1 H2O
33
Aldehyde to carboxylic acid mechanism name, reagent and condition
Oxidation Acidified potassium dichromate , H2SO4 Reflux Uses 1 (O), no H2O
34
Primary alcohol to carboxylic acid mechanism name, reagent and condition
Oxidation Acidified potassium dichromate , H2SO4 Reflux and excess oxidising agent Uses 2(O) and 1H2O
35
Secondary alcohol to ketone mechanism name, reagent and condition
Oxidation Acidified potassium dichromate , H2SO4 Distillation or reflux Uses 1 (O) , produces 1 H2O
36
Aldehyde/ ketone to alcohol mechanism name, reagent and condition 1
Nucleophilic addition NaBH4 Acidic solvent Nucleophile = hydride ion :H-
37
Aldehyde/ ketone to alcohol mechanism 1
Hydride ion attracted to c=o Arrow from middle of double bond to O :O- attracted to H+ that comes from acidic solvent
38
Aldehyde/ ketone to alcohol mechanism name, reagent and condition 2
Nucleophilic addition KCN Acidic solvent Nucleophile = :CN-
39
Aldehyde/ ketone to alcohol mechanism 2
CN ion attracted to c=o Arrow from middle of double bond to O :O- attracted to H+ that comes from acidic solvent Extra carbon
40
Naming on nitriles ( CH3CH2CH(OH)CNCH3) with OH
Longest chain with CN 2- hydroxy-2-methylbutanenitrile
41
Why can’t nucleophilic addition of aldehydes and asymmetrical ketones result in a racemic mixture of optical isomers ?
1. Bonding about a carbonate group in an aldehyde and ketone is planar - 120 degrees 2. This means there is a 50-50 chance of nucleophile attacking molecule on either side 3.This result in equal portions of equal isomer forming a racemic mixture 4. Not optically active as isomers rotate around a plane of polarise that night and cancel each other out
42
Primary alcohol and carboxylic acid mechanism name, reagent and condition
Esterification by condensation reaction Reversible reaction Catalysed by strong acid Removal of OH from carboxylic acid and H from alcohol to form ester
43
Naming of esters
First part after c-o Second part before c=o
44
Esters to carboxylic acid/ alcohol mechanism name, reagent and condition 1
Hydrolysis using H2O Reversible reaction Catalysed by strong acid at room temperature Add OH back onto carboxylic acid and H onto alcohol
45
Esters to carboxylic acid/ alcohol mechanism name, reagent and condition 2
Base catalysed hydrolysis by warm aqueous NaOH Add ONa to carboxylic acid and H to alcohol Form soap such as sodium ethanoate
46
Acyl chloride to carboxylic acid mechanism, reagent
Nucleophilic addition elimination With H2O Lone pair on water attracted to C=O Arrow from middle of c= to O Arrow from middle of c-cl to cl Oxygen attaches on carbon and becomes positive Arrow from middle of O-H to O Lone pair of Oxygen O:- to c-o bond to form double carbon bond Forms HCl
47
Acyl chloride to ester mechanism and reagent
Nucleophilic addition elimination With alcohol Lone pair on oxygen of alcohol attracted to C=O Arrow from middle of c= to O Arrow from middle of c-cl to cl Oxygen attaches on carbon and becomes positive Arrow from middle of O-H to O Lone pair of Oxygen O:- to c-o bond to form double carbon bond Forms HCl
48
Acyl chloride to amide mechanism and reagent
Nucleophilic addition elimination With NH3 ( ammonia) Lone pair on nitrogen attracted to C=O Arrow from middle of c= to O Arrow from middle of c-cl to cl NH3 attaches on carbon and becomes positive Arrow from middle of H to positive N Lone pair of Oxygen O:- to c-o bond to form double carbon bond Forms HCl but also form NH4Cl as side product
49
Acyl chloride to N- substituted amide mechanism and reagent
Nucleophilic addition elimination With amide Lone pair on N attracted to C=O Arrow from middle of c= to O Arrow from middle of c-cl to cl Amide attaches on carbon and becomes positive Arrow from middle of hydrogen to positive N Form HCl but ammonium chloride salt formed as by product Lone pair of Oxygen O:- to c-o bond to form double carbon bond
50
Name CH3CONH2
Ethanamide
51
Name CH3CONHCH3
N-methyl ethanamide
52
Acid anhydride mechanism
2 possible organic products depending on what group nucleophile attacks Nucleophilic attracted to c=o
53
Why are Acylation of acid anhydride more commonly used than Acyl chloride
No HCl fumes produced which are corrosive Cheaper Don’t react with water
54
Nitration forming nucleophile
1. H2SO4 donates a proton to HNO3 HNO3+H204=H2N03+ + HS04- 2. Protonated nitric acid losses a water molecule to form NO2+ which is the electrophile H2NO3+=H20+NO2+
55
Benzene to nitrobenzene mechanism, reagents and conditions
Electrophilic substitution Reagents = concentrated H2SO4 AND HNO3 Arrow from ring of delocalised electrons to N+O2 Hooveshape curve with + inside H coming of and attracted to + to form ring of delocalised electrons C6H5NO2 and H+ used to reform H2SO4
56
Friedel-crafts acylation formation of halogen carrier
Halogen carrier reacts with the haloalkane and takes the halogen atom off haloalkane leaving the alkane CH3Cl + AlCI3=C+H3 + AlCI4-
57
Friedel-crafts acylation mechanism and reagents
Reagents = AlCl3 catalyst and Acyl chloride Arrow from ring of delocalised electrons to CO+CH3 Hooveshape curve with + inside H coming of and attracted to + to form ring of delocalised electrons C6H5COCH3 and H+ used to reform AlCl3
58
Formation of AlCl3 catalyst
H+ + AlCl4- = AlCl3 + HCl
59
Name C6H5COCH3
Phenylethanone
60
Nitrobenzene to amide
HCl and tin catalyst Uses 6(H+) and produces 2H2O

CHEMISTRY ⚗️⚛️🧪 (21 decks)

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