Ch 17 Alcohols

Question 1

Synthesis of Alcohols: Reduction of carbonyl compounds: Aldehydes

Answer 1

1) NaBH4 or LiAlH4/ 2) H2SO4

Results in primary alcohol

Question 2

Synthesis of Alcohols: Reduction of carbonyl compounds: Ketones

Answer 2

1) NaBH4 or LiAlH4/ 2) H2SO4

results in secondary alcohol

Question 3

Synthesis of Alcohols: Reduction of carbonyl compounds: Esters

Answer 3

1) LiAlH4/ 2) H2SO4

results in primary alcohol

Question 4

Synthesis of Alcohols: Reduction of carbonyl compounds: Carboxylic Acids

Answer 4

1) LiAlH4/ 2) H2SO4

results in primary alcohol

Question 5

Synthesis of Alcohols: Grignard addition to carbonyl compounds: Formaldehyde

Answer 5

1) R’MgBr, ether/ 2) H2SO4

results in a primary alcohol

Question 6

Synthesis of Alcohols: Grignard addition to carbonyl compounds: Aldehydes

Answer 6

1) R’MgBr, ether/ 2) H2SO4

Results in a secondary alcohol

Question 7

Synthesis of Alcohols: Grignard addition to carbonyl compounds: Ketones

Answer 7

1) R’MgBr, ether/ 2) H2SO4

results in tertiary alcohol

Question 8

Synthesis of Alcohols: Grignard addition to carbonyl compounds: Esters

Answer 8

1) R’MgBr, ether/ 2) H2SO4

results in tertiary alcohol and R’‘OH as a byproduct

Question 9

Reactions of Alcohols: Dehydration: Tertiary Alcohols

Answer 9

H2SO4

Results in an alkene

Question 10

Reactions of Alcohols: Dehydration: Secondary and tertiary alcohols

Answer 10

POCl3, pyridine

Results in an alkene

Question 11

Reactions of Alcohols: Oxidation: Primary alcohols

Answer 11

PCC, CH2Cl2

Primary alcohol –> aldehyde

CrO3/ H2SO4, acetone

Primary alcohol –> carboxylic acid

Question 12

Reactions of Alcohols: Oxidation: secondary alcohols

Answer 12

PCC, CH2Cl2

secondary alcohols –> ketone