10. Addition Reactions

What is the major product obtained from the addition of HBr to each of the following compounds?

a.

b.

What is the major product obtained from the addition of HBr to each of the following compounds?

e.

f.

What will be the product of the preceding reaction if HBr is used in place of Br₂?

What is the major product of the reaction of each of the following with HBr?

c.

d.

When 1-chlorocyclohexene reacts with HBr, the major product is 1-bromo-1-chlorocyclohexane. Propose a mechanism for this reaction, and explain why your proposed intermediate is more stable than the other possible intermediate

Propose mechanisms consistent with the following reactions.

(c)

(a) Based on what you know about the relative stabilities of alkyl cations and benzylic cations, predict the product of addition of HBr to 1-phenylpropene.

(b) Propose a mechanism for this reaction.

Show how hex-1-yne might be converted to

e. 2-bromohexane.

Limonene is one of the compounds that give lemons their tangy odor. Show the structures of the products expected when limonene reacts with an excess of each of these reagents.

(i) hydrogen bromide gas in a solution containing dimethyl peroxide

When 3-methyl-1-butene reacts with HBr, two alkyl halides are formed: 2-bromo-3-methylbutane and 2-bromo-2-methylbutane. Propose a mechanism that explains the formation of these two products.

Predict the product of the following haloalkane syntheses.

(c) HBr↗HOOH

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (iii) HBr, H₂O₂

(g)

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (iii) HBr, H₂O₂

(k)

(a) How would you convert propene to 2-bromopropane?