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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

Expert verified

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

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

a)

b)

Compound A, C10H18O, undergoes reaction with dilute H2SO4at 50 掳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

Evidence that cleavage of 1,2-diols by HIO4occurs through a five membered cyclic periodate intermediate is based on kinetic data鈥攖he measurement of reaction rates. When diols A and B were prepared and the rates of their reaction withHIO4were measured, it was found that diol A cleaved approximately 1 million times faster than diol B. Make molecular models of A and B and of potential cyclic periodate intermediates, and then explain the kinetic results

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.

Hydroxylation of cis-2-butene with OsO4yields a different product than hydroxylation of trans-2-butene. Draw the structure, show the stereochemistry of each product, and explain the difference between them.
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