Chapter 18: Q19P (page 945)
Give the structures of the carbonyl compound and the amine used to form the following imines.
(a)

(b)

(c)

(d)

(e)

(f)

Short Answer
(a)

(b)

(c)

(d)

(e)

(f)

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Chapter 18: Q19P (page 945)
Give the structures of the carbonyl compound and the amine used to form the following imines.
(a)

(b)

(c)

(d)

(e)

(f)

(a)

(b)

(c)

(d)

(e)

(f)

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Show how would you accomplish the following syntheses. You may use whatever additional reagents you need.
(a)

(b)

(c)

(d)

(e)

(f)

Predict the products formed when cyclopentanone reacts with the following reagents.
(a) CH3NH2 , H+
(b) excess CH3OH , H+
(c) hydroxylamine and weak acid
(d) ethylene glycol and p-toluenesulfuric acid
(e) phenylhydrazine and weak acid
(f) PhMgBr and then mild H3O+
(g) Tollens reagent
(h) sodium acetlylide, then H3O+
(i) hydrazine, then hot. fused KOH
(j) Ph3P=CH2
(k) sodium cyanide
(l) acidic hydrolysis of the product from (k)
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
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
Show how you would synthesize the following derivatives from appropriate carbonyl compounds



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