Question

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

Answer 1

Answer: (A)

(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:
$\underset{4-chloro-2-hydroxy-3-butene-1-oicacid}{\underset{4}{\stackrel{\begin{array}{c}Cl\\ |\end{array}}{\mathrm{CH}}}=\underset{3}{C}H-\stackrel{\begin{array}{c}OH\\ |\end{array}}{\underset{2}{C}H}-\underset{1}{C}OOH}$
$\underset{\begin{array}{c}4-chloro-3-hydroxy-3-butene\\ -1-oicacid\end{array}}{\stackrel{\begin{array}{c}Cl\\ |\end{array}}{\mathrm{CH}}=\stackrel{\begin{array}{c}OH\\ |\end{array}}{C}-C{H}_2-COOH}$
(iv) It can also show functional isomerism as functional isomer of an alcohol is ether.
$\underset{alcohol}{\stackrel{\begin{array}{c}Cl\\ |\end{array}}{\mathrm{CH}}=CH\stackrel{\begin{array}{c}OH\\ |\end{array}}{\mathrm{CH}}COOH}$
$\underset{ether}{\stackrel{\begin{array}{c}Cl\\ |\end{array}}{\mathrm{CH}}=CHOC{H}_{2}COOH}$