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Chapter 9: Q73P (page 451)

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

a. methoxycyclohexane

b. cyclohexylmethylamine

c. dicyclohexyl ether

Short Answer

Expert verified

c.

Step by step solution

01

How SN1 reaction proceed

1. It is a two step reaction.

2. In this carbocation is formed.

3. In this negative ion will attack from the side where there is less number of bulkier groups.

4. As the carbocation intermediate is formed so the stability order 3掳 carbocation>2掳 carbocation>1掳 carbocation

02

Final answer

A large excess of methylamine will have to be used in the second step in order to minimize the formation of a tertiary Amine and a quarternary ammonium ion.

c.Half of the cyclohexene is converted to bromocyclohexane and half is converted to an alkoxide ion. The ether is formed from the reaction of bromocyclohexane with the alkoxide ion.

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Most popular questions from this chapter

a. Assuming that the two compounds shown below have the same stability, which one would you expect to be more reactive in an SN1 reaction?

b. Draw the products that each would form when the solvent is ethanol.

Why do cis-1-bromo-2-ethylcyclohexane and trans-1-bromo-2-ethylcyclohexane form different major products when they undergo an E2 reaction?

Does increasing the energy barrier for an SN2 reaction increase or decrease the magnitude of the rate constant for the reaction?

Rank the following species in each set from best nucleophile to poorest nucleophile.

a. Propose a mechanism for the following reaction.

b. Explain why two products are formed.

c. Explain why methanol substitutes for only one of the bromines.
See all solutions

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