General Organic ChemistryMedium

Question

Given below are two statements:

Statement (I) : Benzyl chloride reacts faster in $S_{N}1$ mechanism than ethyl chloride.

Statement (II) : Ethyl carbocation intermediate is less stabilized by hyperconjugation than benzyl carbocation by resonance.

In the light of the above statements, choose the correct answer from the options given below :

Options

A.Both Statement I and Statement II are true
B.Both Statement I and Statement II are false
C.Statement I is true but Statement II is false
D.Statement I is false but Statement II is true

Solution

Sol. [Key Concept: $S_{N}1$ rate $\propto$ carbocation stability; benzyl$+$ (resonance) $>$ ethyl$+$ (hyperconjugation).]

Rate of ${SN}^{1} \propto$ Stability of carbocation Order of stability of carbocation :

$$Ph - \overset{\oplus}{C}H_{2} > {CH}_{3} - \overset{\oplus}{C}H_{2} $$Hyperconjugation in ${CH}_{3} - \overset{\oplus}{C}H_{2}$

Resonance in $Ph - \overset{\oplus}{C}H_{2}$

Create a free account to view solution

View Solution Free
Topic: General Organic Chemistry·Practice all General Organic Chemistry questions

More General Organic Chemistry Questions

Methyl - α - D - glucoside and methyl - β - D - glucoside are :...Which of the following correctly shows the order of decreasing basicity -...Which one of the following is the most acidic?...Arrange the following in Increasing of their basicity OH−, CH3COO− CI− I II III...Different hydrogens in a b b c d e f CH3CH = CH−CH2−CH2−CH(CH3)2 are represented by alphabets. Arrange...