Two alkenes,X (91% yield) and Y (9% yield),ar | vedclass

Name: Exam Paper Generator | JEE NEET Paper Generator | Vedclass
Brand: Vedclass
Rating: 5 (35 reviews)

Question

(C) The reaction is a Hoffmann elimination (also known as the Cope elimination if an amine oxide is used,but here it is a quaternary ammonium hydroxid

Vedclass · Accepted Answer

methylenecyclopentane and $1-$methylcyclopentene

Vedclass · Answer

(C) The reaction is a Hoffmann elimination (also known as the Cope elimination if an amine oxide is used,but here it is a quaternary ammonium hydroxide). In Hoffmann elimination,the less substituted alkene (the one with fewer alkyl groups on the double-bonded carbons) is the major product because the bulky leaving group (trimethylamine) prefers to abstract a proton from the less sterically hindered $\beta$-carbon. $1$. The starting material is $1$-methylcyclopentyltrimethylammonium hydroxide. $2$. The $\beta$-hydrogens are available on the ring carbons adjacent to the quaternary nitrogen. $3$. Removing a proton from the $CH_2$ group adjacent to the quaternary center leads to the formation of methylenecyclopentane (the less substituted,Hoffmann product). $4$. Removing a proton from the $CH$ group (the tertiary carbon) leads to the formation of $1$-methylcyclopentene (the more substituted,Zaitsev product). Since Hoffmann elimination favors the less substituted alkene as the major product,$X$ $(91\%)$ is methylenecyclopentane and $Y$ $(9\%)$ is $1$-methylcyclopentene. Therefore,the correct option is $(C)$.

Two alkenes,$X$ ($91\%$ yield) and $Y$ ($9\%$ yield),are formed when the following compound is heated:
The structures of $X$ and $Y$,respectively,are:

Similar Questions

Which of the compounds with molecular formula $C_5H_{10}$ yields acetone on ozonolysis?

For the given reaction:
(Cyclohexyl)-$CH$=$CH$-(Cyclohexyl) $\xrightarrow{KMnO_4/H^+}$ '$P$' (major product)
'$P$' is:

An alkene on ozonolysis gave acetaldehyde. The alkene is:

What is the product formed by the vigorous oxidation of $(CH_3)_2C=CHCH_2CH_3$ with a permanganate solution?

Ozonolysis of compound $X$ followed by reduction yields two moles of the same aldehyde. What is $X$?

Vedclass Test Series

Exam Paper Generator

Online Exam Module

Two alkenes,$X$ ($91\%$ yield) and $Y$ ($9\%$ yield),are formed when the following compound is heated:The structures of $X$ and $Y$,respectively,are: