O CHEM FINAL EXAM

Question 1

Primary alcohol to aldehyde

Answer 1

PCC, CH2Cl2 / DMP, CH2Cl2 / 1) DMSO, (COCl)2 2) Et3N

Question 2

Alkene to aldehyde

Answer 2

1) O3 2) DMS&raquo_space; Ozonolysis

Question 3

Terminal alkyne to aldehyde

Answer 3

1)R2BH 2) H2O2, NaOH&raquo_space; Hydroboration-Oxidation

Question 4

Secondary alcohol to ketone

Answer 4

Na2Cr2O7, H2SO4,H2O

Question 5

Alkene to ketone

Answer 5

1) O3 2) DMSO&raquo_space; Ozonolysis

Question 6

Terminal alkyne to ketone

Answer 6

H2SO4, H2O, HgSO4

Question 7

Benzene to Benzanone

Answer 7

Acid halide (Cl), AlCl3&raquo_space; Friedel-Crafts Acylation

Question 8

Aldehyde/ Ketone to diol

Answer 8

-OH/H3O, H2O&raquo_space; Base/Acidic hydration

Question 9

Aldehyde/ Ketone to acetal

Answer 9

2ROH, TsOH, C6H6, heat

Question 10

Aldehyde/ Ketone to imine

Answer 10

RNH2, TsOH

Question 11

Aldehyde/ Ketone to enamine

Answer 11

R2NH, TsOH

Question 12

Aldehyde/ Ketone to 3* alcohol

Answer 12

RMgBr, (CH3CH2)2O, H3O+

Question 13

Aldehyde/ Ketone to cyanohydrin

Answer 13

HCN, pH 10

Question 14

Aldehyde to carboxylic acid

Answer 14

Peracids&raquo_space; Baeyer-Villiger oxidation

Question 15

Ketone to ester

Answer 15

Peracids