Chapter 21: 5P (page 817)
Give the IUPAC name for each ketone
a.

b

c

Short Answer
a. 2-cyclohexylpentan-3-one
b. 3-tert-butyl-2-methylcyclopentanone
c. 2,2,4,4-tetramethylpentan-3-one
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Chapter 21: 5P (page 817)
Give the IUPAC name for each ketone
a.

b

c

a. 2-cyclohexylpentan-3-one
b. 3-tert-butyl-2-methylcyclopentanone
c. 2,2,4,4-tetramethylpentan-3-one
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Give the IUPAC name (including any E,Z designation) for each unsaturated aldehyde. Neral is obtained from lemon grass, and cucumber aldehyde (Problem 1.30) contributes to the aroma of a fresh mango.
a.

b.

Draw a stepwise mechanism for the following reaction that converts a dicarbonyl compoundto a furan.
Outline a synthesis of each Wittig reagent from Ph3P and an alkyl halide.
a.

b.

c.

Consider the para-substituted aromatic ketones, NO2C6H4COCH2 (p-nitroacetophenone) and CH3OC6H4COCH3 (p-methoxyacetophenone).
a. Which carbonyl compound is more stable?
b. Which compound forms the higher percentage of hydrate at equilibrium?
c. Which compound exhibits a carbonyl absorption at a higher wavenumber in its IR spectrum?
Explain your reasoning in each part.
Label each compound as an acetal, a hemiacetal, or an ether.
a.

b.

c.

d.

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