Chapter 22: 58E (page 752)
How would you synthesize the following compounds from cyclohexanone?
More than one step may be required.

Short Answer
a)

b)

c)

d)

e)

f)

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Chapter 22: 58E (page 752)
How would you synthesize the following compounds from cyclohexanone?
More than one step may be required.

a)

b)

c)

d)

e)

f)

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Rank the following compounds in order of increasing acidity:

When a ketone is treated with acid and a halogen, the a-monohalogenated product can be obtained in high yield. However, under basic conditions it is extremely difficult to isolate the mono halogenated product. Provide an explanation for this reactivity.
Predict the product(s) of the following reactions:

Which of the following substances would undergo the haloform reaction?
(a)CH3COCH3 (b) Acetophenone (c) CH3CH2CHO
(d)CH3CO2H (e)
When optically active (R)-2-methylcyclohexanone is treated with either aqueous base or acid, racemization occurs. Explain.
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