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Photochemical chlorination of (CH3)3CCH2C(CH3)3 gave a mixture of two monochlorides in a
Chapter 8, Problem 8.27(choose chapter or problem)
Photochemical chlorination of \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{3}\) gave a mixture of two monochlorides in a 4:1 ratio. The structures of these two products were assigned on the basis of their \(\mathrm{S}_{\mathrm{N}} 1\) hydrolysis rates in aqueous ethanol. The major product (compound A) underwent hydrolysis much more slowly than the minor one (compound B). Deduce the structures of compounds A and B.
Questions & Answers
QUESTION:
Photochemical chlorination of \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{3}\) gave a mixture of two monochlorides in a 4:1 ratio. The structures of these two products were assigned on the basis of their \(\mathrm{S}_{\mathrm{N}} 1\) hydrolysis rates in aqueous ethanol. The major product (compound A) underwent hydrolysis much more slowly than the minor one (compound B). Deduce the structures of compounds A and B.
ANSWER:Step 1 of 3
\(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{3}\) was photochemically chlorinated, resulting in a 4:1 combination of two monochlorides. Based on their rates of hydrolysis in aqueous ethanol, the structures of these two products were determined. Compound A, the primary product, hydrolyzed significantly more slowly than compound B, the minor product.