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Give the structural formula of an unsatu...

Give the structural formula of an unsaturated hydrocarbon with the lowest number of `C` atoms (or with lowest molecular mass) which shows:
a. Optical isomers
b. Geometrical isomers
c. Both optical and geometrical isomers

Text Solution

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a) An unsaturated hydrocarbon with lowest molecular mass should have one `(C-=C)`, one `(C=C)`,

Due to presence of stereocenter this compound shows optical isomerism.
b) Geometrical isomerism is shown by the `(C=C)` only and not by `(C-=C)`, so we have an alkene of the type

In this, one `R` group should have `(C-=C)` and the other `R` should be a `Me` group so that the lowest number of `C` atoms is obtained

c) In compound `(A)` given in the solution to part `(a)`, put one `Me` group at `C-1` so that it can show both geometrical and optical isomerism.

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i. (A), a compound with lowest number of C atoms, is unsaturated hydrocarbon and is optically active. ii. (B), a compound with lowest number of C atoms, is unsaturated hydrocarbon and shows diastereomerism. iii. (C), a compound with lowest number of C atoms and unsaturated hydrocarbon, shows both optical and geometrical isomerism. Following is the reaction sequence of A, B, and C. The structure of compound (A) is:

Formula For The Number Of Optical Isomers