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Chapter 8: Q2P (page 222)

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

Short Answer

Expert verified

The five alkene products formed are shown below.

Step by step solution

01

Dehydration with aqueous sulfuric acid

The dehydration of alcohol in acid catalyst removes water from the alcohol and forms an alkene product.H2SO4Is 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 , 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

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?

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?

Compound A, C10H18O, undergoes reaction with dilute H2SO4at 50 °C to yield a mixture of two alkenes, C10H16. The major alkene product, B, gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Identify A and B, and write the reactions.

Cyclopentanone

What product would you expect from the reaction of cyclopentene with NBS and water? Show the stereochemistry.

Question:Predict the products of the following reactions, showing both regiochemistry and stereochemistry where appropriate:

(d)

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