Alcohols

Question 1

Synthesis

Answer 1

Oxymercuration: Hg(OAc)2, H2O / NaBH4
Hydroboration: BH3 / H2O2, OH-

Question 2

Functional group

Answer 2

1. Add halogen
2. Take away halogen (OR-) > makes double bond
3. Add H3O+ > alcohol

Question 3

Grignard formaldehyde

Answer 3

H2C=O > RCH2OH

Primary

Question 4

Acetaldehyde

Answer 4

CH3-CH=O > RC(-OH)H-CH3

Secondary

Question 5

Ketone

Answer 5

R1-C(=O)-R2 > R1-(OH-)C(R)-R2

Tertiary

Question 6

Acid chloride

Answer 6

R-C(=O)-Cl > R-C(-R1)=O

*doubling reagent = 2x R1

Question 7

Ester

Answer 7

R-C(=O)-R1 > R-(R2-)C(-OH)-R1

*double reagent = 2x R2

Question 8

CO2

Answer 8

R-C(=O)-OH

Question 9

Oxides

Answer 9

CH2(^O-)CH2 > R-CH2-CH2-OH

Primary, 2 extra carbons

Question 10

Synthesis by reduction

Answer 10

Aldehyde: RCH2OH primary
Ketone: R-CH(-OH)-R1 secondary

Question 11

LiAlH4

Answer 11

RCH2OH (primary)