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Chapter 9: Q109P (page 391)

Two bromoethers are obtained from the reaction of the following alkyl dihalide with methanol. Draw the structures of the ethers.

Short Answer

Expert verified

The structures formed in this reaction are given below

Step by step solution

01

Reaction pathway

The above compound has two different Br which form two secondary carbocations among which the carbocation breaking the 1st C-Br bond is stabilized through resonance. So, this centre will undergo reaction following both SN1 and SN2 mechanism.

The C-Br bond considering the 2nd Br atom produces a secondary carbocation which is not resonance stabilised. So, it will undergo substitution reaction following SN2 mechanism.

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Most popular questions from this chapter

a. Which reacts faster in an SN2 reaction?

b.Which reacts faster in an E1 reaction?

c.Which reacts faster in an SN1 reaction?

What products are formed when the following stereoisomer of 2-chloro-1,3-dimethylcyclohexane reacts with methoxide ion?

a. Explain why the reaction of an alkyl halide with ammonia gives a low yield of primary amine.

b. Explain why a much better yield of primary amine is obtained from the reaction of an alkyl halide with an azide ion (-N3), followed by catalytic hydrogenation. (Hint: An alkyl azide is not nucleophilic.)

Predict the product for the following reaction and write a mechanism to explain how it is formed.

How does the ratio of substitution product to elimination product formed from the reaction of propyl Bromide with CH3O- in methanol change if the nucleophile is changed to CH3S-?
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