ORGANIC SYNTHESIS

Question 1

carboxylic acid to alcohol

Answer 1

LiAlH4 (dry ether)
reduction

Question 2

carboxylic acid to acyl chloride

Answer 2

PCl5
dry conditions

Question 3

carboxylic acid to ester

Answer 3

Alcohol + H2SO4
heat + reflux

Question 4

carboxylic acid to carboxylate salt

Answer 4

metals or base reaction

Question 5

acyl chloride to alcohol

Answer 5

LiAlH4 (dry ether)
reduction

Question 6

acyl chloride to sub amide

Answer 6

Amine

Question 7

acyl chloride to amide

Answer 7

Conc Ammonia

Question 8

acyl chloride to ester

Answer 8

Alcohol
Dry conditions

Question 9

ester to carboxylate salt + alcohol

Answer 9

NaOH
heat + hydrolysis

Question 10

ester to protonated carboxylic acid + alcohol

Answer 10

HCl
heat + hydrolysis

Question 11

alkene to alkane

Answer 11

nickel catalyst
steam, 200 degrees
hydrogenation

Question 12

alkene to haloalkane

Answer 12

H-X (br, cl)
addition

Question 13

alkene to diol

Answer 13

acidic KMnO4
addition

Question 14

alkene to poly(alkene)

Answer 14

zieger-natter catalyst
heat and high pressure
radical mechanism

Question 15

haloalkane to alkene

Answer 15

warm NaOh in ethanol
elimination

Question 16

haloalkane to nitrile

Answer 16

KCN in ethanol
heat + reflux
substitution

Question 17

haloalkane to amine

Answer 17

excess alcoholic ammonia
heat in sealed tube
substitution

Question 18

haloalkane to alcohol

Answer 18

warm NaOH in water
hydrolysis
substitution

Question 19

alkane to alkene

Answer 19

zeolite catalyst
heat
cracking

Question 20

alkane to haloalkane

Answer 20

diatomic halogen (Cl2 / Br2)
radical sub

Question 21

alcohol to alkoxide

Answer 21

Na
Acid-base

Question 22

alcohol to chloroalkane

Answer 22

PCl5 (s) or PCl3

Question 23

alcohol to bromoalkane

Answer 23

KBr + 50% H2SO4
Heat

Question 24

alcohol to Iodoalkane

Answer 24

Red Phosphorus + Iodine
Heat

Question 25

Alkene to Alcohol

Answer 25

- steam - high heat high pressure

Question 26

Alcohol to Alkene

Answer 26

- H3PO4 - dehydration - elimination

Question 27

Halogenoalkane + aldehyde to increase chain length

Answer 27

HCN and KCN reflux heat

Question 28

Nitrile to COOH

Answer 28

- dilute aqueous HCL - hydrolysis - reflux heat

Question 29

nitrile to amine

Answer 29

LiAlH4 dry ether

Question 30

grignard reagent

Answer 30

haloalkane + Mg Reflux Dry Ether + dil HCL to end product

Question 31

grignard reagent + methanal

Answer 31

- primary alcohol

Question 32

grignard reagent + -nal

Answer 32

secondary alcohol

Question 33

grignard reagent + ketone

Answer 33

tertiary alcohol

Question 34

grignard reagent + Co2

Answer 34

carboxylate acid