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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


The structures of three monomers are shown. In each case, show the structure of the polymer that would result from polymerization of the monomer. Vinyl chloride is polymerized to 鈥樷�檝inyl鈥欌�� plastics and PVC pipe. Tetrafluoroethylene polymerizes to Teflon, used as non-stick coatings and PTFE valves and gaskets. Acrylonitrile is polymerized to Orlon, used in sweaters and carpets.

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

Sketch the expected proton NMR spectra of 3,3- dimethylbutanal.

Question: Show how you would accomplish the following conversions.

(a)Cis-hex-3-ene to meso-hexane-3,4-diol

(b)Cis-hex-3-ene to (d,l)-hexane-3,4-diol

(c)Trans-hex-3-ene to meso-hexane-3,4-diol

(d)Trans-hex-3-ene to (d,l)-hexane-3,4-diol

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

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