Chapter 12: Q13P (page 354)
Show how you could prepare the following compounds from 4-methyl-3- penten-2-one,
(a)

(b)

(c)

Short Answer
(a)

Formation of the desired product
(b)

Formation of the desired product
(c)

Formation of the desired product
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Chapter 12: Q13P (page 354)
Show how you could prepare the following compounds from 4-methyl-3- penten-2-one,
(a)

(b)

(c)

(a)

Formation of the desired product
(b)

Formation of the desired product
(c)

Formation of the desired product
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Question: 21-65 Propose a structure for a compound, , that has the following
IR and1H NMR spectra:

Assign R or S stereochemistry to the two chirality centers in isocitrate, and tell whether OH and H add to the Si face or the Re face of the double bond.
Question: The mass spectrum (a) and the infrared spectrum (b) of another unknown hydrocarbon are shown. Propose as many structures as you can.


Reaction of acetone with yields hexadeuterioacetone. That is, all the hydrogens in acetone are exchanged for deuterium. Review the mechanism of mercuric-ion-catalyzed alkyne hydration, and then propose a mechanism for this deuterium incorporation.

Question: Two infrared spectra are shown. One is the spectrum of cyclohexane,
and the other is the spectrum of cyclohexene. Identify them, and
explain your answer.
(a)

(b)

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