Show by means of reactions, how you will inter-convert cis-trans isomers of hex-3-ene?
A
1. Br2/CCl4; 2.NaNH2/NH3 3. LindlarPd/CH2 for cis; Li,NH3 for trans
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B
1. Br2/CCl4; 2.NaNH2/NH3 3. LindlarPd/CH2 for trans; Li,NH3 for cis
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C
1. Br2/CCl4; 2.NaNH2/NH3 3. LindlarPd/CH2 for trans; Na,NH3 for cis
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D
1. Br2/CCl4; 2.NaNH2/NH3 3. LindlarPd/CH2 for cis; Na,NH3 for trans
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Solution
The correct option is D 1. Br2/CCl4; 2.NaNH2/NH3 3. LindlarPd/CH2 for cis; Na,NH3 for trans Start with any isomer and bromine addition across the double bond of hex-3-ene gives 3,4-dibromohexane.
From the above compound, get to hex-3-yne by dehydrohalogenation:
Getting to hex-3-yne is the key. From there it is easy!