Give plausible explanation for each of the following:
$(i)$ Cyclohexanone forms cyanohydrin in good yield but $2,2,6-$trimethylcyclohexanone does not.
$(ii)$ There are two $-NH_2$ groups in semicarbazide. However,only one is involved in the formation of semicarbazones.
$(iii)$ During the preparation of esters from a carboxylic acid and an alcohol in the presence of an acid catalyst,the water or the ester should be removed as soon as it is formed.

Vedclass pdf generator app on play store
Vedclass iOS app on app store
(N/A) $(i)$ Cyclohexanone forms cyanohydrin because the nucleophile $CN^{-}$ can easily attack the carbonyl carbon without significant steric hindrance. In $2,2,6-$trimethylcyclohexanone,the methyl groups at the $\alpha-$positions create significant steric hindrance,preventing the nucleophilic attack of $CN^{-}$.
$(ii)$ Semicarbazide $(H_2N-NH-CO-NH_2)$ exhibits resonance where the lone pair of electrons on one of the $-NH_2$ groups is delocalized towards the carbonyl group. This reduces the electron density and nucleophilicity of that specific $-NH_2$ group. The other $-NH_2$ group,which is not involved in resonance,remains nucleophilic and attacks the carbonyl carbon of aldehydes and ketones to form semicarbazones.
$(iii)$ The esterification reaction between a carboxylic acid and an alcohol is a reversible process: $RCOOH + R'OH \rightleftharpoons RCOOR' + H_2O$. According to Le Chatelier's principle,removing the products (water or ester) as they are formed shifts the equilibrium in the forward direction,thereby increasing the yield of the ester.

Explore More

Similar Questions

Match the reactions given in Column-$I$ with their names in Column-$II$.
Column-$I$ (Reaction) Column-$II$ (Name)
$A$. $RCH_2COOH \rightarrow[H_2O]{X_2/P} RCH(X)COOH$ $i$. Decarboxylation
$B$. $RCOONa \rightarrow[NaOH, CaO, \Delta]{\text{soda lime}} RH$ $ii$. Grignard reaction
$C$. $RCOOH + R'OH \leftrightarrow{H^{+}} RCOOR' + H_2O$ $iii$. Hell-Volhard-Zelinsky reaction
$D$. $RMgX + R'CHO \rightarrow{H_3O^{+}} RCH(OH)R'$ $iv$. Esterification

Difficult
View Solution

Provide identification tests for the following pairs of compounds:
$(1)$ Phenol and carboxylic acid
$(2)$ Formic acid and acetic acid
$(3)$ Acetic acid and ethanol
$(4)$ Acetic acid and acetone
$(5)$ Aldehyde and ketone
$(6)$ Acetaldehyde and acetone
$(7)$ Acetaldehyde and formaldehyde
$(8)$ Benzaldehyde and acetaldehyde

Identify the major product of the reaction when the given compound is hydrolyzed and heated strongly.

Difficult
View Solution

The major product expected when Phthalamide is treated with $NaOH$ is:

Difficult
View Solution

Which $\beta$-keto acid shown will not undergo decarboxylation?

Vedclass Products

For Students

Vedclass Test Series

Mock tests in real JEE/NEET style with performance analysis. 5-day free trial.

Start Free Trial
For Teachers

Exam Paper Generator

Generate Set A/B/C/D exam papers from 7.5L+ questions in 2 minutes. 3 chapters free.

Try Free
For Institutes

Online Exam Module

Live online exams with unlimited students, 360° analytics & white-label branding.

See Demo