Chapter 17 Review Sheet I.

Predict the products of the following reactions:

O 1.NaBH4, MeOH 2.H3O+ O H 1.LiAlH4 / ether 2.H3O+ CH2OH OH

O OCH2CH3 O OH 1. NaBH4/MeOH 2. H3O+ Mg 1.LiAlH4 2.H3O+ OH

N.R.
(CH3)2C=O OMgBr H 3O + OH

Br

MgBr

A
O OCH3 1.CH3CH2MgBr 2.H3O+ OH

Br OH O

Mg

N.R.

1.CH3MgBr 2.H3O+ NH2 POCl3

N.R.

OH

Br TMS-Cl N(Et)3

Br Mg OTMS

OH MgBr 1.(CH3)2C=O 2.H3O+

OH

OTMS

OTMS

Cl

OH

DHP, H3O+

Cl

NaOH HO

A
O PCC H O O H 3O + O H

B
OH

C
OH

K2Cr2O7

N.R.

OH HO OH

CrO3, H3O+ HO

O OH

OH HO OH OH HIO4 OH

PCC H

O OH

O H O H

OH

KOH

O - K+

CH3CH2Cl

II. Provide mechanisms for the following transformations:

OH OH a) H+ OH OH2+ O O-MgBr+ H OH2+ OH H 3O + O O b) 1.CH3MgBr 2.H3O+ CH3MgBr OH

OH

OH

III. Perform the following syntheses using only the indicated organic starting materials, PCC, TMS-Cl, and any inorganic materials or your choice.
a) ??? O

OH

OH PCC O H +

1. PBr3 2. Mg

MgBr

2. H3O+ MgBr OH

OH

PCC

b)

???

1. Br2, hv 2. Mg MgBr + O

MgBr

1. Br2, hv 2. H2O, H3O+ OH

OH

PCC

2. H3O+

c)

???

1.NaBH4, MeOH 2.H3O+

OH

1. SOCl2 2. Mg

MgCl

1.

2. H3O+ 3. H2SO4

d) HO Br

???

O HO 1. LiAlH4 2. H3O+ PCC H O

HO

Br 1. TMSCl NEt3 2. Mg

HO

TMSO

MgBr + O

O H KF

2. H3O+

OH TMSO

PCC

O HO

TMSO

*Other blocking groups such as tert-butanol or dihydropyran may be used instead of TMS.