Alcohols

Question 1

Answer 1

1) BH₃ THF

———————–>

2) H₂O₂, NaOH

Question 2

Answer 2

1) Hg(OAc)₂

———————->

2) NaBH₄

Mercury prevents rearrangement

Question 3

Answer 3

H₃O⁺

Rearrangement has occured

Question 4

Answer 4

1) OsO₄

—————–>

2) NaHSO₃

syn dihydroxylation

Question 5

Answer 5

1) mCPBA

——————–>

2) H₃O⁺

anti-dihydroxylation

Question 6

Answer 6

This is a reduction of a ketone.

Weaker reducing agent:

NaBH₄ (source of H^-)

————————–>

MeOH (source of H⁺)

Stronger reducing agent:

1) LAH (source of H^-)

—————————->

2) H₂O (Source of H⁺)

Question 7

Answer 7

This is reduction of an aldehyde.

Weaker reducing agent:

NaBH4 (source of H-)

————————–>

MeOH (source of H+)

Stronger reducing agent:

1) LAH (source of H-)

—————————->

2) H2O (Source of H+)

Question 8

Answer 8

This is reduction of a carboxylic acid.

Harder to reduce, use the stronger hydride reducing agent.

1) LAH (source of H-)

—————————->

2) H2O (Source of H+)

Question 9

Answer 9

Question 10

Answer 10

Question 11

Answer 11

Question 12

Answer 12

H₂, Pt

Hight temp, high pressure

Question 13

Answer 13

1) CH₃MgBr

——————->

2) H₂O

Question 14

Answer 14

HBr

hydroboration, Sn1 process

Question 15

Answer 15

PBr₂

(Sn2)

Question 16

Answer 16

SOCl₂

—————–>

Py

(Sn2)

Question 17

Answer 17

TsCl

—————>

Py

(Sn1)