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Chapter 16: Q52P (page 784)
Question: Draw the structure for each of the following:
a.
b.
c.
d.
ANSWER
a
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Question: Show two ways to convert an alkyl halide into a carboxylic acid that has one more carbon than the alkyl halide.
Propose a mechanism for each of the following reactions:
Draw the structure for each of the following:
a. isobutyraldehyde
b. 4-hexenal
c. diisopentyl ketone
d. 3-methylcyclohexanone
e. 2,4-pentanedione
f. 4-bromo-3-heptanone
g. -bromocaproaldehyde
h. 2-ethylcyclopentanecarbaldehyde
i. 4-methyl-5-oxohexanal
The pKa of protonated acetone is about -7.5, and the pKa of protonated hydroxylamine is 6.0.
a. In a reaction with hydroxylamine at pH 4.5 (Figure 16.2), what fraction of acetone is present in its acidic, protonated form? (Hint: See Section 2.10.)
b. In a reaction with hydroxylamine at pH 1.5, what fraction of acetone is present in its acidic, protonated form?
c. In a reaction with acetone at pH 1.5 (Figure 16.2), what fraction of hydroxylamine is present in its reactive basic form?
Question:Explain why aldehydes and ketones react with a weak acid such as hydrogen cyanide but do not react with strong acids such as HCl or H2SO4 (other than being protonated by them).
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