Organic Synthesis Routes

Question 1

Carboxylic Acid to Ester

Answer 1

Alcohol + Conc. H2SO4
Heat
Esterification

Question 2

2° Alcohol to Ketone

Answer 2

K2Cr2O7/H+ (Acidified Potassium Dichromate)
Heat and Reflux
Oxidation

Question 3

Alcohol to Ester

Answer 3

Carboxylic acid + Conc H2SO4 OR Acid Anhydride
Heat
Esterification

(Esters and amides can be hydrolysed by NaOH and acids)

Question 4

Nitrile OR Hydroxynitrile to Carboxylic Acid

Answer 4

H2O, HCl
Heat

Question 5

Alkene to Dihalogenoalkane

Answer 5

Br2, Cl2
Room Temp
Electrophilic Addition

Question 6

Acyl Chloride / Acid Anhydride to Ester

Answer 6

Alcohol
Room Temp
Nucleophilic Addition Elimination

Question 7

Aldehyde to Alcohol

Answer 7

NaBH4
Reduction
Nucleophilic Addition

Question 8

Acyl Chloride / Acid Anhydride to 2° Amide

Answer 8

1° Amine
Room Temp
Nucleophilic Addition Elimination

Question 9

Alkene to Halogenoalkane

Answer 9

Hydrogen Halide (HBr, HCl)
Room Temp
Electrophilic Addition

Question 10

Alkene to Alkane

Answer 10

H2/Ni

Question 11

Acyl Chloride / Acid Anhydride to Carboxylic Acid

Answer 11

H2O
Room Temp
Nucleophilic Addition Elimination

Question 12

Alkene to Polyalkene

Answer 12

High Pressure Catalyst

Question 13

Ketone to Alcohol

Answer 13

NaBH4
Reduction
Nucleophilic Addition

Question 14

Nitrile to 1° Amine

Answer 14

LiAlH4 in ether OR H2/Ni
Reduction

Question 15

Alcohol to Alkene

Answer 15

Conc. H2SO4 OR Conc. H3PO4
Heat
Elimination
Dehydration

Question 16

Halogenoalkane to Alkene

Answer 16

KOH Alcoholic
Heat under Reflux
Elimination

Question 17

Ketone to Hydroxynitrile

Answer 17

NaCN + H2SO4
Nucleophilic Addition

Question 18

Aldehyde to Hydroxynitrile

Answer 18

NaCN + H2SO4
Nucleophilic Addition

Question 19

Aldehyde to Carboxylic Acid

Answer 19

(If primary) K2Cr2O7/H+ (Acidified Potassium Dichromate)
Heat under Reflux + Excess Oxidising Agent
Oxidation

Question 20

Alcohol to Carboxylic Acid

Answer 20

K2Cr2O7/H+ (Acidified Potassium Dichromate)
Heat and Reflux
Oxidation

Question 21

Halogenoalkane to 1° Amine

Answer 21

Alcoholic NH3
Heat under Pressure
Nucleophilic Substitution

Question 22

Halogenoalkane to Alcohol

Answer 22

KOH OR NaOH Aqueous
Heat under Reflux
Nucleophilic Substitution

Question 23

Carboxylic Acid to Acyl Chloride

Answer 23

SOCl2

Question 24

Primary Amine to 2°, 3° or 4° Amine

Answer 24

Halogenoalkane
Nucleophilic Substitution

Question 25

Dihalogenoalkane to Diol

Answer 25

Aqueous KOH
Heat under Reflux
Nucleophilic Substitution

Question 26

Acyl Chloride / Acid Anhydride to 1° Amide

Answer 26

NH3
Room Temp
Nucleophilic Addition Elimination

Question 27

Alcohol to Haloalkane

Answer 27

Sodium Halide
H2SO4

Question 28

Hydroxynitrile to Amine

Answer 28

H2/Ni

Question 29

1° Alcohol to Aldehyde

Answer 29

K2Cr2O7/H+ (Acidified Potassium Dichromate)
Heat and Distill
Partial Oxidation

Question 30

Alkane to Halogenoalkane

Answer 30

Br2, Cl2
UV light
Free Radical Substitution

Question 31

1° Amine to 2° Amide

Answer 31

Acyl chloride
Room temp
Nucleophilic Addition Elimination

Question 32

Halogenoalkane to Nitrile

Answer 32

KCN in ethanol / water mixture
Heat under Reflux
Nucleophilic Substitution

Question 33

Alkene to Alcohol

Answer 33

Step 1:
H2SO4 / H3PO4
Electrophilic Addition

Step 2:
H2O
Warm
Hydrolysis

Question 34

Ester to Carboxylate

Answer 34

OH-
Heat

Question 35

Ester to Carboxylic Acid

Answer 35

Dilute Acid
Heat