Chapter 18: Q16P (page 942)
Show how you would accomplish the following synthesis.
(a) Acetphenone→ acetophenone cyanohydrin
(b) Cyclopentancarbaldehyde→ 2-cyclopentyl-2-hydroxyacetic acid
(c) Hexan-1-ol →2-hydroxyheptanoic acid
Short Answer


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Chapter 18: Q16P (page 942)
Show how you would accomplish the following synthesis.
(a) Acetphenone→ acetophenone cyanohydrin
(b) Cyclopentancarbaldehyde→ 2-cyclopentyl-2-hydroxyacetic acid
(c) Hexan-1-ol →2-hydroxyheptanoic acid


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Which of the following compounds would give a positive Tollens test? (Remember that the Tollens test involves mild basic aqueous conditions)
(a) CH3CH2COCH3
(b) CH3CH2CHO
(c) CH3CH2CH=CHCH=CHOH
(d) CH3CH2 CH2CH(OH)OCH3
(e) CH3CH2 CH2CH(OCH3)2
(f)

Predict the major products of the following reactions:
(a) (b)

(c) (d)

Use equations to show the fragmentation leading to each numbered peak in the mass spectrum of octane-2-one .

Name the following ketones and aldehydes. When possible, give both a common name and an IUPAC name.
(j) (k) (l)
Propose mechanisms for
(a) the acid-catalyzed hydration of chloral to form chloral hydrate.
(b) the base-catalyzed hydration of acetone to form acetone hydrate
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