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Chapter 8: Q8-2P. (page 222)

Question: How many alkene products, including E, Z isomers, might be obtained by dehydration of 3-methyl-3-hexanol with aqueous sulfuric acid?

Short Answer

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Answer

The five alkene products formed are,

Step by step solution

01

Dehydration with aqueous sulfuric acid

The dehydration of alcohol in acid catalyst H2SO4removes water from the alcohol and forms an alkene product. H2SO4 Is a good dehydrating agent and is very good at removing water from the compounds.

02

The formation of alkene products

When 3-methyl-3-hexanol is dehydrated with aqueous H2SO4, it removes water (OH and H group). The five alkene products obtained are E/Z-3-Methyl-3-hexene, E/Z-3-Methyl-2-hexene and 2-Ethyl-1-pentene.

Formation of alkene products

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Most popular questions from this chapter

Using an oxidative cleavage reaction, explain how you would distinguish between the following two isomeric dienes:

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

a)

b)

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

(a) Cyclopentene and cyclopentane

An unknown hydrocarbon A with the formula C6H12 reacts with 1 molar equivalent ofH2 over a palladium catalyst. Hydrocarbon A also reacts withOsO4 to give diol B. When oxidized withKMnO4 in acidic solution, A gives two fragments. One fragment is propanoic acid, CH3CH2CO2H, and the other fragment is ketone C. What are the structures of A, B, and C? Write all reactions, and show your reasoning.

Question: In planning the synthesis of one compound from another, it鈥檚 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.
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