Rxns

Question 1

Convert alkene to alkane

Answer 1

H2 + cat (hydrogenation)

Question 2

Convert alkyne to alkane

Answer 2

H2 + Wilkinson’s Catalyst RhCl(PPh3)

Question 3

Convert imine to amine

Answer 3

H2 + cat (hydrogenation)

Question 4

Convert aldehyde/ketone to alcohol

Answer 4

H2 + cat (difficult) (hydrogenation) or reduce with NaBH4

Question 5

Cleave O-Ph bond

Answer 5

H2 + cat (hydrogenolysis)

Question 6

Cleave N-Ph bond

Answer 6

H2 + cat (hydrogenolysis)

Question 7

Convert alkyne to alkene

Answer 7

H2 + Lindlar’s Catalyst (Pd, CaCO3, Pb)

Question 8

Convert carboxylic acid, ester, or acyl chloride to alcohol

Answer 8

LiAlH4 x2 (reduction)

Question 9

Convert ester to aldehyde

Answer 9

DIBALH (reduction)

Question 10

Convert amide to amine

Answer 10

LiAlH4 x2 (reduction)

Question 11

Convert nitrile to amine

Answer 11

LiAlH4 x2 (reduction)

Question 12

Convert aldehyde/ketone to amine

Answer 12

RNH2, NaBH3(CN) (convert to imine, then reduce)

Question 13

Convert alcohol to carboxylic acid

Answer 13

K2Cr2O7, KMnO4, etc. (oxidation)

Question 14

Convert alcohol to aldehyde

Answer 14

PCC (oxidation)

Question 15

Convert alcohol to ketone

Answer 15

Any oxidant

Question 16

Convert tertiary alcohol to carbonyl compound

Answer 16

Impossible

Question 17

Reaction of two carbonyl groups

Answer 17

Likely aldol (enolate + ketone) forming ketone+hydroxyl or ketone +alkene w excess base added

Question 18

Create a multi-aromatic system

Answer 18

Suzuki-Miyaura, Negishi, Stille cross-couplings, or Ullman, Heck, Buchwald-Hartwig condensation/cross-coupling like.

Question 19

Add amine to aryl group

Answer 19

PhCHO (reductive amination), haloaryl + amine + pd cat