Advices For Studying Organic Chemistry

C

C

CH 3

CH 3

2-Butyne

1. Li,EtNH 2


2. NH 4 Cl
   anti addition of H 2

C

C

H CH 3

H 3 H

trans-2-Butene

3) Synthesis of 2-butyne:

C

Retrosynthetic Analysis

H 3 CCCCH 3 H 3 CCC −Na+ + CH 3 I

H 3 CCC −Na+ H 3 CCCH+ NaNH (^2)
Synthesis
H 3 CCCH1. NaNH2. CH 3 I^2 /liq. NH^3 H 3 CCCCH 3
4) Synthesis of propyne:
Retrosynthetic Analysis
HCCCH 3 HCC −Na+ + CH 3 I
Synthesis
HCCH1. N2. CHaNH^2 /liq. NH^3
3 I HCCCH^3

The Chemistry of Cholesterol Biosynthesis: Elegant and Familiar

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