question_answer

The compound\[CHCl=CHCHOHCOOH\] with molecular formula\[{{C}_{4}}{{H}_{5}}{{O}_{3}}Cl\] can exhibit

A)  geometric, optical, position and functional isomerism

B)  geometric, optical and functional isomerism

C)  position and functional isomerism only

D)  geometric and optical isomerism only

E)  geometric isomerism only

Correct Answer: A

Solution :

(i) Geometrical   isomers   of   compound \[CHCl=CHCHOHCOOH\] (ii) It also shows optical isomerism as (iii) It can also show position isomerism. For example two positional isomers are given below: \[\underset{4\text{ }-chloro-2-hydroxy\text{ }-3-butene\text{ }-1\text{ }-oic\text{ }acid}{\mathop{\underset{4}{\overset{\begin{smallmatrix}  Cl \\  | \end{smallmatrix}}{\mathop{CH}}}\,=\underset{3}{\mathop{C}}\,H-\overset{\begin{smallmatrix}  OH \\  | \end{smallmatrix}}{\mathop{\underset{2}{\mathop{C}}\,H}}\,-\underset{1}{\mathop{C}}\,OOH}}\,\] \[\underset{\begin{smallmatrix}  4-chloro-3-hydroxy-3-butene \\  \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,-1-oic\text{ }acid \end{smallmatrix}}{\mathop{\overset{\begin{smallmatrix}  Cl \\  | \end{smallmatrix}}{\mathop{CH}}\,=\overset{\begin{smallmatrix}  OH \\  | \end{smallmatrix}}{\mathop{C}}\,-C{{H}_{2}}-COOH}}\,\] (iv) It can also show functional isomerism as functional isomer of an alcohol is ether. \[\underset{alcohol}{\mathop{\overset{\begin{smallmatrix}  Cl \\  | \end{smallmatrix}}{\mathop{CH}}\,=CH\overset{\begin{smallmatrix}  OH \\  | \end{smallmatrix}}{\mathop{CH}}\,COOH}}\,\] \[\underset{ether}{\mathop{\overset{\begin{smallmatrix}  Cl \\  | \end{smallmatrix}}{\mathop{CH}}\,=CHO\text{ }C{{H}_{2}}\text{ }COOH}}\,\]