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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

Draw the substitution products for each of the following reactions; if the products can exist as stereoisomers, show what stereoisomers are obtained:

a. ( R )-2-bromopentane + CH3O-

b. ( R )-3-bromo-3-methylheptane + CH3OH

c. benzyl chloride + CH3CH2OH

d. allyl chloride + CH3OH

e. 1-bromo-2-butene + CH3O-

f. 1-bromo-2-butene + CH3OH

a. Identify the substitution products that form when 2-bromo-2-methylpropane is dissolved in a mixture of 80% ethanol and 20% water.

b. Explain why the same products are obtained when 2-chloro-2-methylpropane is dissolved in a mixture of 80% ethanol and 20% water.

Indicate which species in each pair gives a higher substitution-product-to-elimination-product ratio when it reacts with isopropyl bromide:

a. ethoxide ion or tert-butoxide ion

b. -OCN or -SCN

c. Cl- or Br-

d. CH3S- or CH3O-

Propose a mechanism for the following reaction:

Which alkyl halide in each pair is more reactive in an E2 reaction with hydroxide ions?
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