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Chapter 8: 8-7b (page 230)

What products would you expect from oxymercuration-demercuration of the following alkenes?

a)

b)

Short Answer

Expert verified

b) The product obtained from oxymercuration-demercuration of alkene is,


Step by step solution

01

Oxymercuration-Demercuration procedure

Oxymercuration in an electrophilic addition reaction in whichto an alkene, when alkene is treated with Hg(OAc)2.This intermediate organomercury compound is further treated with and the last step involves the demercuration to form an alcohol.

02

The product obtained from oxymercuration-demercuration of alkene

b) In this alkene, oxymercuration results in the Markovnikov addition of to an alkene. Here, the OH is added to that carbon which is more substituted, and H is added to that carbon which is less substituted.


The product obtained from oxymercuration-demercuration of alkene

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Most popular questions from this chapter

Question: What product would you expect to obtain from addition of to 1,2-dimethyl-cyclohexene? Show the stereochemistry of the product.

Compound A has the formula C10H16. On catalytic hydrogenation over palladium, it reacts with only 1 molar equivalent of H2. Compound A also undergoes a reaction with ozone, followed by zinc treatment, to yield a symmetrical diketone, B(C10H16O2).

What are the structures of A and B?

Question:How would you carry out the following transformations? Tell what

reagents you would use in each case.

(a)

From what alkenes might the following alcohols have been prepared?

a)

Reaction of HBr with 3-methylcyclohexene yields a mixture of four products: cis- and trans-1-bromo-3-methylcyclohexane and cis- and trans-1-bromo-2-methylcyclohexane. The analogous reaction of HBr with 3-bromocyclohexene yields trans-1,2-dibromocyclohexane as the sole product. Draw structures of the possible intermediates, and then explain why only a single product is formed in this reaction.
See all solutions

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