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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

Which of the following reactions take place more rapidly when the concentration of the nucleophile is increased?

Starting with cyclohexene, how could the following compounds be prepared?

a. methoxycyclohexane

b. cyclohexylmethylamine

c. dicyclohexyl ether

Explain how the following changes affect the rate of the reaction of 2-bromo-2-methylbutane with methanol:

a. The alkyl halide is changed to 2-chloro-2-methylbutane.

b. The alkyl halide is changed to 2-chloro-3-methylbutane.

a. Draw the structures of the products obtained from the reaction of each enantiomer of cis-1-chloro-2-isopropylcyclopentane with sodium methoxide in methanol.

b. Are all the products optically active?

c. How would the products differ if the starting material were the trans isomer? Are these products optically active?

d. Will the cis enantiomers or the trans enantiomers form substitution products more rapidly?

e. Will the cis enantiomers or the trans enantiomers form elimination products more rapidly?

The pKa of acetic acid in water is 4.76. What effect will a decrease in the polarity of the solvent have on the pKa? Why?
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