Organic Synthesis

Question 1

Alkene to Alkane

Answer 1

• H2
• nickel catalyst
• 150 c
• 5 atm
• addition reaction

Question 2

alkene to haloalkane

Answer 2

• hydrogen halide
• room temp
• addition reaction

Question 3

alkene to alcohol

Answer 3

• steam
• 300 c
• 60 atm
• H3PO4 concentrated
• addition reaction

Question 4

alkane to haloalkane

Answer 4

• halogen
• UV light
• substitution reaction

Question 5

haloalkane to alcohol

Answer 5

• NaOH
• reflux
• substitution reaction

Question 6

haloalkane to nitrile

Answer 6

• KCN
• ethanolic solution
• reflux
• substitution reaction

Question 7

haloalkane to amine

Answer 7

• concentrated NH3
  heated in sealed tube
  substitution reaction

Question 8

carboxylic acid to acyl chloride

Answer 8

SOCl3
PCl3/PCl5
reflux
substitution reaction

Question 9

alcohol to aldehyde

Answer 9

primary
Cr2O72-
H+
distil
oxidation reaction

Question 10

alcohol to ketone

Answer 10

secondary
Cr2O72-
H+
reflux
oxidation reaction

Question 11

alcohol to carboxylic acid

Answer 11

primary
Cr2O72-
H+
reflux
oxidation reaction

Question 12

aldehyde to carboxylic acid

Answer 12

Cr2O72-
H+
reflux
oxidation reaction

Question 13

ketone to alcohol

Answer 13

LiAlH4 in dry ether
reduction

Question 14

aldehyde to alcohol

Answer 14

LiAlH4 in dry ether
reduction

Question 15

carboxylic acid to alcohol

Answer 15

LiAlH4 in dry ether
reduction

Question 16

nitrile to amine

Answer 16

LiAlH4 in dry ether
reduction

Question 17

amide to amine

Answer 17

LiAlH4 in dry ether
reduction

Question 18

haloalkane to alkene

Answer 18

hot concentrated KOH
alcoholic solution
elimination

Question 19

alcohol to alkene

Answer 19

H2SO4 concentrated
reflux
elimination

Question 20

amide to nitrile

Answer 20

P3O5
distil
elimination

Question 21

alcohol to ether

Answer 21

primary only
H2SO4
heat
elimination

Question 22

carboxylic acid to acid anhydride

Answer 22

P3O5
distil
elimination

Question 23

nitrile to carboxylic acid

Answer 23

aqueous H+
H2O
reflux
hydrolysis

Question 24

amide to carboxylic acid

Answer 24

H2SO4
heat
hydrolysis

Question 25

acyl chloride to carboxylic acid

Answer 25

H2O hydrolysis

Question 26

acid anhydride to carboxylic acid

Answer 26

H2O reflux hydrolysis

Question 27

ester to carboxylic acid

Answer 27

reflux H+ or OH- hydrolysis

Question 28

nitrile to amide

Answer 28

H2O acid/ base catalyst hydrolysis

Question 29

acyl chloride to amide

Answer 29

concentrated NH3 and room temp= primary amide RNH2, reflux = secondary amide

Question 30

acyl chloride to ester

Answer 30

ROH room temp acylation

Question 31

acid anhydride to ester

Answer 31

ROH anhydrous reflux acylation

Question 32

acid anhydride to amide

Answer 32

NH2 reflux= primary amide RNH2, reflux= secondary amide

Question 33

carboxylic acid to ester

Answer 33

ROH concentrated H2SO4 catalyst esterification

Question 34

alkene to addition polymer

Answer 34

polymerisation

Question 35

alkane to alkene

Answer 35

cracking

Question 36

alkene to alcohol

Answer 36

steam

Question 37

alkene to diol

Answer 37

potassium manganate cold, dilute and acidified

Question 38

alcohol to halogenoalkane (1)

Answer 38

phosphorus halide (e.g. PCl5) produces halegnoalkane, POCl, and HCl (if PCl5 used)

Question 39

alcohol to halogenoalkane (2)

Answer 39

HBr that is formed from 50% concentrated sulfuric acid and KBr

Question 40

alcohol to halgenoalkane (3)

Answer 40

phosphorous iodide formed from red phosphorus and iodine

Question 41

reaction with dehydrating agents

Answer 41

alcohol under reflux phosphoric acid forms alkene