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Chapter 10: PROBLEM 10.59 (page 423)

Question: Draw a stepwise mechanism that shows how all three alcohols are formed from the bicyclic alkene.

Short Answer

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Answer

Step by step solution

01

Stability of carbocation

The formation of the major product of the alkene addition reaction depends on the stability of the carbocation. If the reaction gives secondary and tertiary carbocation intermediates, the tertiary carbocation will form the major product.

02

Explanation

The protonation of alkene occurs in the presence of sulfuric acid to form a secondary carbocation. The tertiary carbocation is generated by 1,2-methyl shift.

The mechanism is shown below:

Reaction mechanism

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Most popular questions from this chapter

Question: Name the alkene depicted in the ball-and-stick model and draw the constitutional isomers formed when the alkene is treated with each reagent: (a) Br2; (b) Br2 inH2O ; (c) Br2 in CH3OH.

Question: Draw the products of each reaction and indicate their stereochemistry.

Question: Devise a synthesis of each product from the given starting material. More than one step is required.

a.

b.

c.

d.

e.

f.

Question: Draw a stepwise mechanism for the following reaction. This reaction combines two processes together: the opening of an epoxide ring with a nucleophile and the addition of an electrophile to a carbon–carbon double bond. (Hint: Begin the mechanism by protonating the epoxide ring.)

Question: Draw the isomers for the following compounds and then name each one:

a. 2-methyl-2,4-hexadiene

b. 2,4-heptadiene

c. 1,3-pentadiene
See all solutions

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