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Question: Answered & Verified by Expert
An alkene $A\left(\mathrm{C}_4 \mathrm{H}_8\right)$ exhibits cis/trans isomerism. $A$ on ozonolysis gives $B$, which when reacted with $\mathrm{NaOH}$ followed by hydroxylamine gave $C$. What are $B$ and $C$ ?
ChemistryHydrocarbonsTS EAMCETTS EAMCET 2020 (11 Sep Shift 2)
Options:
  • A $\begin{array}{cc}\mathbf{B} & \mathbf{C} \\ \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CHO} & \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}==\mathrm{NOH}\end{array}$
  • B $\begin{array}{cc}\mathbf{B} & \mathbf{C} \\ \mathrm{CH}_3 \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CHO} & \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}=\mathrm{CHCH} \mathrm{CH}_2=\mathrm{NOH}\end{array}$
  • C $\begin{array}{cc}\mathbf{B} & \mathbf{C} \\ \mathrm{CH}_3 \mathrm{CHO} & \mathrm{CH}_3 \mathrm{CH}=\mathrm{CHCH}=\mathrm{NNH}_2\end{array}$
  • D $\begin{array}{cc}\mathbf{B} & \mathbf{C} \\ \mathrm{CH}_3 \mathrm{CHO} & \mathrm{CH}_3 \mathrm{CH}=\mathrm{CHCH}=\mathrm{NOH}\end{array}$
Solution:
2484 Upvotes Verified Answer
The correct answer is: $\begin{array}{cc}\mathbf{B} & \mathbf{C} \\ \mathrm{CH}_3 \mathrm{CHO} & \mathrm{CH}_3 \mathrm{CH}=\mathrm{CHCH}=\mathrm{NOH}\end{array}$


Here, $(B)$ is $\mathrm{CH}_3 \mathrm{CHO}$
and $(C)$ is $\mathrm{CH}_3 \mathrm{CH}==\mathrm{CHCH}=\mathrm{NOH}$.
(i) On ozonolysis double bond get broken to give $\mathrm{CH}_3 \mathrm{CHO}$.
(ii) On reaction with $\mathrm{NaOH}$ followed by hydroxyl amine, we get
$\mathrm{CH}_3-\mathrm{CH}=\mathrm{CHCH}=\mathrm{NOH}$

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