Some Organic Synthesis Practice Problems: Starting from 1 ...

Some Organic Synthesis Practice Problems:

Starting from 1-hexene, 1-butyne, bromoethane, iodomethane and any reagent needed (you do not need to use all of these compounds), synthesize:

1.

Cl Cl

CHCl3, KOH

Li, NH3

H3C C C CH2CH3 NaNH2, NH3, CH3I

H C C CH2CH3

2.

3.

octane

O H

1) BH3 2) NaOH, H2O2

H2O

H3CH2CH2CH2C C CH

NaNH2

Br2 Br

Br

H2, Pd

H3CH2CH2CH2C C C CH2CH3

NaNH2, NH3 CH3CH2Br H3CH2CH2CH2C C CH see above

4.

OH

1) OsO4

2) NaHSO3

OH (racemic)

HO

OH

H H

Li, NH3 H3CH2C C C CH2CH3

NaNH2, NH3 CH3CH2Br

H3CH2C C CH 1-butyne

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