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Chapter 20: Q29P (page 1038)

Show how Gabriel synthesis are used to prepare the following amines.

  1. benzylamine (b) hexane-1-amine (c) 蠏-amino butyric acid

Short Answer

Expert verified

Here potassium phthalimide is used as amine synthon and allowing preparation of primary amine by reaction of alkyl halide with benzyl chloride.

(a)

(a)

(b)

(b)

(c)

(c)

Step by step solution

01

Gabriel synthesis of benzyl amine

Here potassium phthalimide is used as amine synthon and allowing preparation of primary amine by reaction of alkyl halide with benzyl chloride.

02

Gabriel synthesis of hexane-1-amine

Here potassium phthalimide is used as amine synthon and allowing preparation of primary amine by reaction of alkyl halide with benzyl chloride.

03

Gabriel synthesis of ϒ-amino butyric acid

Here potassium phthalimide is used as amine synthon and allowing preparation of primary amine by reaction of alkyl halide with benzyl chloride.

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Most popular questions from this chapter

(a)Hydrogen peroxide (HOOH) has a pKa of 11.6, making it roughly 10,000 times as strong an acid as water (pKa = 15.7). Explain why H2O2is a stronger acid than H2O.

(b) In contrast to part (a), peroxyacetic acid (pKa = 8.2) is a much weakeracid than acetic acid (pka = 4.74) . Explain why peroxyacetic acid is a weaker acid than acetic acid.

(c) Peroxyacetic acid (bp = 105掳 C) has a lower boiling point than acetic acid (bp = 118掳 C) , even though peroxyacetic acid has a higher molecular weight. Explain why peroxyacetic acid is more volatile than acetic acid.

There are three dioxane isomers: 1,2-dioxane, 1,3- dioxane, and 1,4-dioxane. One of these acts like an ether and is an excellent solven for Grignard reactions. Another one is potentially explosive when heated. The third one quickly hydrolyzes in dilute acid. Show which isomer acts like a simple ether, and then explain why one of them is potentially explosive. Propose a mechanism for the acid hydrolysis of the third isomer.

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(a)trans-1-产谤辞尘辞产耻迟-2-别苍别鈫�trans-pent-3-enoic acid (two ways)

(b)hex-3-ene鈫抪ropanoic acid

(c) but-2-enal鈫抌ut-2-enoic acid

(d) hexanoic acid鈫抙exanal

(e)

(f)

(g)

(h)

For each compound,

  1. Classify the nitrogen containing functional groups.
  2. Provide acceptable name

(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)

Predict the compound in each pair that will undergo solvolysis (in aqueous ethanol) more rapidly.

(a)

(b)

(c)

(d)

(e)

(f)
See all solutions

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