4 Synthetic Routes

Question 1

Haloalkane to alcohol

Answer 1

NaOH (aq) (or water or ammonia???)
Reflux
(Halogen is replaced by -OH. Makes Sodium halide)

Question 2

Alkane to haloalkane

Answer 2

Halogen/UV
Haloalkane and hydrogen halide
E.g. bromomethane and HBr
Radical substitution 
Initial stage
Propagation
Termination

Question 3

Alkene to haloalkane

Answer 3

Hydrogen halide or halogen
Electrophilic addition
Curly arrow from double bond to electropositive atom. Single bond to electroneg atom.

Question 4

Alkene to alkane

Answer 4

H2
Ni catalyst
423Kelvin (150oC)

Question 5

Alkene to alcohol

Answer 5

H2O(g) (steam)
H3PO4 catalyst
Hydration

Question 6

Alcohol to haloalkane

Answer 6

Sodium halide
H2SO4
Substitution reaction
Sodium halide + sulfuric acid -> NaHSO4 + Hydrogen halide
The hydrogen halide produced is used in reaction
Alcohol + hydrogen halide -> haloalkane + H2O
Produces water

Question 7

Alcohol to alkene

Answer 7

Dehydration
Water molecule removed
Heated under reflux in presence of phosphoric acid catalyst

Question 8

Primary alcohol to carboxylic acid

Answer 8

K2Cr2O7/H2SO4 
Heated under Reflux 
Oxidation
Alcohol + 2[O] -> carboxylic acid + H2O
Produces water
The dichromate ions change colour from orange to green

Question 9

Primary Alcohol to aldehyde

Answer 9

K2Cr2O7/H2SO4
Distilled
Oxidation
Alcohol + [O] -> aldehyde + water
Produces water

Question 10

Secondary alcohol to ketone

Answer 10

K2Cr2O7/H2SO4
Heated under reflux
Oxidation
Alcohol + [O] -> Ketone + water
Produces water
The dichromate ions change colour from orange to green

Question 11

haloalkane to nitrile

Answer 11

NaCN

ethanol

Question 12

haloalkane to amine

Answer 12

NH3

ethanol

Question 13

primary alcohol to ester

Answer 13

carboxylic acid

conc H2SO4

Question 14

nitrile to amine

Answer 14

H2

Ni catalyst

Question 15

nitrile to carboxylic acid

Answer 15

H2O
HCl
heat
forms carboxylic acid and NH4Cl

Question 16

carboxylic acid to ester

Answer 16

alcohol

conc H2SO4

Question 17

carboxylic acid to acyl chloride

Answer 17

SOCl2

produces acyl chloride + SO2(g) + HCl(g)

Question 18

aldehyde to primary alcohol

Answer 18

NaBH4/H2O

Question 19

aldehyde to carboxylic acid

Answer 19

K2CR2O7/H2SO4

reflux

Question 20

aldehyde to hydroxynitrile

Answer 20

HCN

H2SO4/NaCN

Question 21

ester to carboxylic acid and alcohol

Answer 21

dil acid hydrolysis
H+/H2O
heat

Question 22

ester to sodium salt of COOH and alcohol (carboxylate)

Answer 22

NaOH/H2O
alkaline hydrolysis
heat

Question 23

acyl chloride to ester

Answer 23

alcohol

Question 24

acyl chloride to carboxylic acid

Answer 24

H2O

Question 25

acyl chloride to primary amide

Answer 25

NH3

Question 26

acyl chloride to secondary amide

Answer 26

primary amine

Question 27

benzene to nitrobenzene

Answer 27

HNO3 H2SO4 50oC

Question 28

nitrobenzene to phenylamine

Answer 28

Sn/conc HCl | NaOH?????

Question 29

phenylamine to tribromophenylamine

Answer 29

Br2

Question 30

benzene to bromobenzene

Answer 30

Br2 | FeBR3

Question 31

benzene to chlorobenzene

Answer 31

Cl2 | AlCl3

Question 32

benzene to methylbenzene

Answer 32

CH3Cl | AlCl3

Question 33

benzene to benzene ketone ?? | C6H5COCH3

Answer 33

CH3COCl | AlCl3

Question 34

phenol to nitrophenol

Answer 34

dil HNO3

Question 35

phenol to sodiumphenoxide

Answer 35

NaOH(aq)

Question 36

phenol to tribromophenol

Answer 36

Br2

Question 37

nitrobenzene to bromonitrobenzene

Answer 37

Br2 FeBr3 high temp

Question 38

ROH + NaCl + H2SO4 -->

Answer 38

RCl + NaHSO4 + H2O

Question 39

water in and out of condenser

Answer 39

water in at bottom

Question 40

RCN + acid

Answer 40

RCOOH

Question 41

MP of impure compound

Answer 41

lower than MP of pure compound

Question 42

reason for heating under reflux

Answer 42

to prevent any substances escaping

Question 43

haloalkane + H2O (+AgNO3 + ethanol)

Answer 43

alcohol + AgX

Question 44

radical substitution limitations

Answer 44

further substitution | substitution at diff positions on chain

Question 45

homologous series

Answer 45

same functional groups, diff carbon chain length | each successive member differs by CH2

Question 46

anhydrides and alcohol

Answer 46

ester | anhydrides dont react w carboxylic acids

Question 47

kekule and delocalised model similarities

Answer 47

overlap of p orbitals | pi ring above and below

Question 48

kekule and delocalised model differences

Answer 48

K has alternating pi bonds | delocalised has pi ring