CH 20

Question 1

Synthesis of carboxylic acids

Answer 1

1) benzylic position with KMnO4 or Na2Cr2O7, H2SO4, H20
2) primary alc with Na2Cr2O7, H2SO4, H20
3) terminal alkyne with 1)O3 2)H20
4) aldehyde with Na2Cr2O7, H2SO4, H20
5) alkene with 1)O3 2)H202

Question 2

cyanide to carboxylic acid

Answer 2

H2SO4, H20

Question 3

add COOH to end

Answer 3

1) Mg0
2)CO2
3)H2SO4

*adds 1 C

Question 4

carboxylic acid to primary alc

Answer 4

1)LAH
2)H20

Question 5

selective reduction of carboxylic acids

Answer 5

BH3 THF

Question 6

carboxylic acid to acyl chloride

Answer 6

SOCl2, pyr

Question 7

acyl chloride to carboxylic acid

Answer 7

H20

Question 8

acyl chloride to ester

Answer 8

alcohol, pyr

Question 9

acyl chloride to amide

Answer 9

ammonia, primary, or secondary amine

Question 10

acyl chloride to anhydride

Answer 10

carboxylic acid

Question 11

acyl chloride to primary alc

Answer 11

1)LAH
2)H20

Question 12

acyl chloride to aldehyde

Answer 12

Li(tBuO3)AlH, H20

Question 13

what does a gilman do [ (R)2CuLi ] to acyl chloride

Answer 13

Replaces Cl with R (stops at ketone)

Question 14

carboxylic acid to ester

Answer 14

H+, alc

Question 15

esters hydrolyzed to ?? in acidic or basic conditions

Answer 15

carboxylic acids

Question 16

esters to amides

Answer 16

ammonia, primary and secondary amines

Question 17

esters to primary alc

Answer 17

1)LAH
2)H20

Question 18

ester to aldehyde

Answer 18

1) DIBAl-H
2)H20

Question 19

amides are hydrolyzed with H2SO4, H20 to form?

Answer 19

Carboxylic acid and amine

Question 20

amide to secondary amine

Answer 20

1)LAH
2)H20

Question 21

amide replaced with CN

Answer 21

SOCl2 with heat

Question 22

amide replaced with CN

Answer 22

P4O10 with heat

Question 23

nitrile to carboxylic acid

Answer 23

1) KOH, H20, heat
2)H2SO4, H20

Question 24

grignard with nitrile

Answer 24

ketone

Question 25

alpha halogenation of ketones

Answer 25

HX, H20, X2