CH 3- O - CH 2- Cl aq - OH - CH 3- O - CH 2- OH Which information below regarding this reaction is applicable-A- It follows SN 2 pathway- because it is a primary alkyl chlorideB- A mixed S N 1 and S N 2 pathway is followedC- It follows S N 1 pathway- because the intermediate carbocation is resonance stabilizedD- S N 1 pathway is not followed- because the intermediate carbocation is destabilised by -I effect of oxygen-

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Byju's Answer

Standard XII

Chemistry

Reimer Tiemann Reaction

CH 3- O - CH ...

Question

$C H_{3} - O - C H_{2} - C l a q .^{⊖} O H - ---- \to Δ C H_{3} - O - C H_{2} - O H$ Which information below regarding this reaction is applicable?

It follows

S_{N} 2

pathway, because it is a primary alkyl chloride

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It follows

S_{N} 1

pathway, because the intermediate carbocation is resonance stabilized

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S_{N} 1

pathway is not followed, because the intermediate carbocation is destabilised by -I effect of oxygen.

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A mixed

S_{N} 1

and

S_{N} 2

pathway is followed

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Solution

The correct option is B It follows $S_{N} 1$ pathway, because the intermediate carbocation is resonance stabilized
Reaction proceeds via $S_{N} 1$ pathway having stable intermediate. Here intermediate formed is stabilised by +M effect of $O C H_{3}$ group.
$C H_{3} - O - \oplus C H_{2} \leftrightarrow C H_{3} - \oplus O = C H_{2}$

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Similar questions

Q. Which of the following statement(s) is/are true for the following reaction?

(1) It involves a carbocation intermediate
(2) Rearrangement is due to

S_{N} 1

mechanism.
(3) It proceeds via

S_{N} 2

pathway.
(4) It involves neighbouring group participation.

Q. Carbocation intermediate is formed in

S_{N} 1

type of reactions.

Q. Assertion :Phenol is more reactive than benzene towards

O H

B e c a u s e

Reason: In the case of phenol, the intermediate carbocation is more resonance stabilized.

Q. Alkyl halides and alcohols easily undergo nucleophilic substitution either through

S_{N} 1

S_{N} 2

mechanism. The relative case of these two processes depends upon the nature of the substrate (alkyl group) as well as leaving group, nature of nucleophile and also upon the nature of the solvent.

S_{N} 1

mechanism involves the formation of carbocation as intermediate while

S_{N} 2

mechanism involves the formation of a transition pentavalent state.

S_{N} 1

is the main mechanism in

3^{0}

alkyl halides and alcohols, while

S_{N} 2

mechanism is the path adopted by most of the

1^{o}

alkly halides;

2^{o}

alkyl halides may follow

S_{N} 1

as well as

S_{N} 2

What happens when

1^{o} R O H

react with

H X

Q. Assertion:

1^{o}

allylic halides are more reactive than

1^{o} R X

S_{N} 1

reaction
Reason: Allylic carbocation intermediate is stabilised by resonance

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CH3−O−CH2−Claq.⊖OH−−−−−→ΔCH3−O−CH2−OH Which information below regarding this reaction is applicable?

The correct option is B It follows SN1 pathway, because the intermediate carbocation is resonance stabilizedReaction proceeds via SN1 pathway having stable intermediate. Here intermediate formed is stabilised by +M effect of OCH3 group. CH3−O−⊕CH2↔CH3−⊕O=CH2

$C H_{3} - O - C H_{2} - C l a q .^{⊖} O H - ---- \to Δ C H_{3} - O - C H_{2} - O H$ Which information below regarding this reaction is applicable?