Solution Found!
Oxidation of cholesterol converts the alcohol to a ketone.
Chapter 12, Problem 5P(choose chapter or problem)
Oxidation of cholesterol converts the alcohol to a ketone. Under acidic or basic oxidation
conditions, the C = C double bond migrates to the more stable, conjugated position. Before
IR and NMR spectroscopy, chemists watched the UV spectrum of the reaction mixture to
follow the oxidation. Describe how the UV spectrum of the conjugated product, cholest-4-en-
3-one, differs from that of cholesterol.
\(\mathrm{CH}_{3}\)
\(H_{3} C\)
\(\text { HO }\)
Equation transcription:
Text transcription:
{CH}{3}
H{3} C
{ HO }
Questions & Answers
QUESTION:
Oxidation of cholesterol converts the alcohol to a ketone. Under acidic or basic oxidation
conditions, the C = C double bond migrates to the more stable, conjugated position. Before
IR and NMR spectroscopy, chemists watched the UV spectrum of the reaction mixture to
follow the oxidation. Describe how the UV spectrum of the conjugated product, cholest-4-en-
3-one, differs from that of cholesterol.
\(\mathrm{CH}_{3}\)
\(H_{3} C\)
\(\text { HO }\)
Equation transcription:
Text transcription:
{CH}{3}
H{3} C
{ HO }
ANSWER:Solution 5P
Oxidation of cholesterol transforms the alcohol functionality into a ketone. Under these oxidizing conditions, the alkene migrates to a more stable, conjugated position. We’re asked to describe how the UV-VIS spectrum of the oxidized product differs from that of the starting material (cholesterol).