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  4. The compound CHCl=CHCHOHCOOH with molecular formula C4H5O3Cl can exhibit

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Q. The compound $ CHCl=CHCHOHCOOH $ with molecular formula $ {{C}_{4}}{{H}_{5}}{{O}_{3}}Cl $ can exhibit

KEAMKEAM 2011Organic Chemistry – Some Basic Principles and Techniques

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}}\, $

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