Question

In: Chemistry

1) Alpha-amorphene has several allylic sites. Identify them all (Primary allylic carbon, secondary allylic carbon, tertiary...

1) Alpha-amorphene has several allylic sites. Identify them all (Primary allylic carbon, secondary allylic carbon, tertiary allylic carbon)

2) Assume that one allylic hydrogen was removed from alpha-pinene. Draw all the possible resonance structures for the carbaninon that forms. If there is more than one allylic H, Show each one being removed separately.

3) Why are quaternary carbons adjacent to an alkene unable to from suitable resonance structures?

4) Draw all the products fromed by the reaction: beta-santalene ----(NBS,CCl4,ROOR)---->

Solutions

Expert Solution

  1. Alpha-amorphene has several allylic sites. Identify them all (Primary allylic carbon, secondary allylic carbon, tertiary allylic carbon)
  2. Assume that one allylic hydrogen was removed from alpha-pinene. Draw all the possible resonance structures for the carbaninon that forms. If there is more than one allylic H, Show each one being removed separately.
  3. Why are quaternary carbons adjacent to an alkene unable to from suitable resonance structures?

Quaternary carbons are highly electron reach and hybridization of quaternary carbon is sp3. Carbanion with sp3 hybridisation is not energetically stable. Apart from that resonance energy will be so much high that the structures will not be stable.

4.Draw all the products fromed by the reaction: beta-santalene ----(NBS,CCl4,ROOR)---->


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