Chapter 17: Q17-75E (page 567)
Compound A, , has the IR and NMR spectra shown. Proposea structure consistent with the observed spectra, and label each peak inthe NMR spectrum. Note that the absorption at disappears when is added.

Short Answer

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Chapter 17: Q17-75E (page 567)
Compound A, , has the IR and NMR spectra shown. Proposea structure consistent with the observed spectra, and label each peak inthe NMR spectrum. Note that the absorption at disappears when is added.


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Question: Give IUPAC names for the following compounds:






As a rule, axial alcohols oxidize somewhat faster than equatorial alcohols. Which would you expect to oxidize faster, cis-4-tert-butylcyclohexanol or trans-4-tert-butylcyclohexanol? Draw the more stable chair conformation of each molecule.
What products would you expect to obtain from reaction of 1-methylcyclohexanol with the following reagents?
(a) HBr (b) NaH (c) H2SO4 (d) Na2Cr2O7
What alcohols would give the following products on oxidation?
(a)

(b)

(c)

Benzoquinone is an excellent dienophile in the Diels – Alder reaction. What product would you expect from reaction of benzoquinone with 1 equivalent of 1,3 butadiene? From reaction with 2 equivalents of 1,3 butadiene?
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