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

From what alkenes might the following alcohols have been prepared?

b)

Short Answer

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b) The alkene needed to produce given alcohol is,


Step by step solution

01

Conversion of alkene to alcohol

When alkenes undergo oxymercuration-demercuration, it results in the formation of alcohol products.It occurs in two steps, the first step is the treatment of alkene with Hg(AOc)2, and the second step is the reduction with NaBH4.

02

Preparation of alcohol from alkene

b) The given alcohol is prepared by using oxymercuration-demercuration reaction. When vinylcyclohexane is treated with Hg(AOc)2and in the second step, the product is treated with NaBH4. The OH is added to that carbon which is highly substituted.

Formation of alcohol from alkene

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Most popular questions from this chapter

Question:The cis and trans isomers of 2-butene give different cyclopropane productsin the Simmons–Smith reaction. Show the structures of both, and

explain the difference.

What alkenes might be used to prepare the following alcohols by hydroboration-oxidation?

α-Terpinene,C10H16is a pleasant-smelling hydrocarbon that has been isolated from oil of marjoram. On hydrogenation over a palladium catalyst,α-terpinene reacts with two molar equivalentsH2to yield a hydrocarbon, C10H20.On ozonolysis, followed by reduction with zinc and acetic acid,α-terpinene delivers two products, glyoxal, and 6-methyl-2,5- heptane dione.

(a) How many degrees of unsaturation doesα-terpinene have?

(b) How many double bonds and how many rings does it have?

(c) Propose a structure forα-terpinene

Question: In planning the synthesis of one compound from another, it’s just as important to know what not to do as to know what to do. The following reactions all have serious drawbacks to them. Explain the potential problems of each.

Question: One problem with elimination reactions is that mixtures of products are often formed. For example, treatment of 2-bromo-2-methylbutane with KOH in ethanol yields a mixture of two alkene products. What are their likely structures?
See all solutions

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