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Chapter 8: 8-8-a (page 230)

From what alkenes might the following alcohols have been prepared?

a)

Short Answer

Expert verified

a) The alkene used for preparing alcohol is,


Step by step solution

01

Alcohols from alkenes

Alcohols can be prepared from alkenes by using oxymercuration-demercuration reactions.These electrophilic addition reactions are a two-step pathway for obtaining alcohol.

02

Preparation of alcohol from an alkene

a) The given alcohol can be prepared when 2-methylhex-2-ene or 2-methylhex-1-ene is treated with Hg(OAc)2, and water reacts with more substituted carbon. The proton transfer takes place, and at last, demercuration occurs via reduction.


Formation of alcohol as a product

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Most popular questions from this chapter

Which of the reactions below would result in a product mixture thatwould rotate plane-polarized light?

c)

Question: Which of the following alcohols could notbe made selectively by hydroboration–oxidation of an alkene? Explain.

How would you distinguish between the following pairs of compounds using simple chemical tests? Tell what you would do and what you would see.

(b) 2-Hexene and benzene

Compound A, C11H16O, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a palladium catalyst. On treatment of A with dilute sulfuric acid, dehydration occurred and an optically inactive alkene B,C11H14, was the major product. Alkene B, on ozonolysis, gave two products. One product was identified as propanal,CH3CH2CHO. Compound C, the other product, was shown to be a ketone,C8H8O. How many degrees of unsaturation does A have? Write the reactions, and identify A, B, and C.

We’ll see in the next chapter that alkynes undergo many of the same reactions that alkenes do. What product might you expect from each of the following reactions?
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