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A student was studying terpene synthesis, and she wanted
Chapter 9, Problem 37SP(choose chapter or problem)
A student was studying terpene synthesis, and she wanted to make the compound shown here. First she converted 3 -bromo-6-methylcyclohexene to alcohol A. She heated alcohol A with sulfuric acid and purified one of the components (compound B) from the resulting mixture. Compound B has the correct molecular formula for the desired product.
(a) Suggest how 3 -bromo-6-methylcyclohexene might be converted to alcohol A.
(b) The UV spectrum of compound B shows \(\lambda_{n m a x} \text { at } 269 \mathrm{~nm}\). Is compound B the correct product? If not, suggest a structure for compound B consistent with these UV data.
(c) Propose a mechanism for the dehydration of alcohol A to compound B.
Equation Transcription:
Text Transcription:
\lambda_{n m a x} \text { at } 269 \mathrm{~nm}
CH3
Br
CH3
CH3-C-CH3-OH
H2SO4
Questions & Answers
QUESTION:
A student was studying terpene synthesis, and she wanted to make the compound shown here. First she converted 3 -bromo-6-methylcyclohexene to alcohol A. She heated alcohol A with sulfuric acid and purified one of the components (compound B) from the resulting mixture. Compound B has the correct molecular formula for the desired product.
(a) Suggest how 3 -bromo-6-methylcyclohexene might be converted to alcohol A.
(b) The UV spectrum of compound B shows \(\lambda_{n m a x} \text { at } 269 \mathrm{~nm}\). Is compound B the correct product? If not, suggest a structure for compound B consistent with these UV data.
(c) Propose a mechanism for the dehydration of alcohol A to compound B.
Equation Transcription:
Text Transcription:
\lambda_{n m a x} \text { at } 269 \mathrm{~nm}
CH3
Br
CH3
CH3-C-CH3-OH
H2SO4
ANSWER:
Solution 37SP
(a) The 3-bromo-6-methylcyclohexene reacts with Mg metal to form an organometallic compound.
The organometallic compound reacts with acetone followed by hydrolysis to form an alcohol.
