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Chapter 8: Q5P (page 408)

Propose a mechanism to show how 3,3-dimethylbut-1-ene reacts with dilute aqueous H2SO4to give 2,3-dimethylbutan-2-ol and a small amount of 2,3-dimethylbut-2-ene.

Short Answer

Expert verified

3,3-dimethyl-but-1-ene in dilute aqueous acidic conditions undergo protonation on alkene carbon first which leads to the formation of a carbocation intermediate. In the next step, there occurs rearrangement that is, methyl shift, to form the more stable tertiary carbocation.

Formation of carbocation intermediate and methyl shift

Step by step solution

01

Step-1. Formation of carbocation intermediate and methyl shift

3,3-dimethyl-but-1-ene in dilute aqueous acidic conditions undergo protonation on alkene carbon first which leads to the formation of a carbocation intermediate. In the next step, there occurs rearrangement that is, methyl shift, to form the more stable tertiary carbocation.

Formation of carbocation intermediate and methyl shift

02

Step-2. Formation of products 2,3-dimethyl-butan-2-ol and 2,3-dimethyl-but-2-ene

Formation of major and minor products

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Most popular questions from this chapter

Show how you would accomplish each of the following synthetic conversions.

a) Trans-but-2-ene→trans-1,2-dimethylcyclopropane

b) Cyclopentene→

c) Cyclohexanol→

The chiral BINAP ligand shown in figure 8-8 contains no asymmetric carbon atoms. Explain how this ligand is chiral.

Unknown X, C5 H9 Br, does not react with bromine or with dilute KMnO4. Upon treatment with potassium tert-butoxide, X gives only one product, Y, C5 H8. Unlike X, Y decolorizes bromine and changes KMnO4 from purple to brown. Catalytic hydrogenation of Y gives methylcyclobutane. Ozonolysis–reduction of Y gives dialdehyde Z, C5 H8 O2. Propose consistent structures for X, Y, and Z. Is there any aspect of the structure of X that is still unknown?

One of the principal components of lemongrass oil is limonene, C10H16. When limonene is treated with excess hydrogen and a platinum catalyst, the product is an alkane of formulaC10H20. What can you conclude about the structure of limonene?

The chiral BINAP ligand shown in figure 8-8 contains no asymmetric carbon atoms. Explain how this ligand is chiral.
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