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Chapter 20: Q18P a. (page 1065)

Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.

(a)

(b)

(c)

Short Answer

Expert verified

(a)

(b)

(c)

Step by step solution

01

Amines and carboxylic acids

Amines are compounds containing the -NH2group and carboxylic compounds with the 鈥揅OOH group.Different reagents are used to prepare acid derivatives, such as amide HNCH2CH32is used. The formation of amide by using industrial methods needs high temperature.

02

Synthesis of N, N-diethyl-meta-toluamide

(a) When 3-methyl benzoic acid is treated with HNCH2CH32, a carboxylate anion is formed and, on heating, COO-is converted toCONEt2 . The product created is N, N-diethyl-meta-toluamide.


Synthesis of N, N-diethyl-meta-toluamide

03

Synthesis of acetanilide 

(b) When aniline is treated with acetic acid , an acetate ion is formed along with a phenyl ammonium ion. Further, on heating, acetanilide is formed.

04

Reaction of acetanilide 

Synthesis of acetanilide

05

Synthesis of N, N-dimethylformamide(DMF)

(c) When aniline is treated with acetic acid (CH3COOH) , an acetate ion is formed along with a phenyl ammonium ion. Further, on heating, acetanilide is formed.

06

Reaction of N, N-dimethylformamide(DMF) 

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Most popular questions from this chapter

Question:

  1. The Key Mechanism for Fischer esterification omitted some important resonance forms of the intermediates shown in brackets. Complete the mechanism by drawing all the resonance forms of these two intermediates.
  2. Propose a mechanism for the acid-catalyzed reaction of acetic acid with ethanol to give ethyl acetate.
  3. The Principle of Microscopic Reversibility states that a forward reaction and a reverse reaction taking place under the same conditions (as in equilibrium) must follow the same reaction pathway in microscopic detail. The reverse of the Fischer esterification is the acid-catalyzed hydrolysis of an ester. Propose a mechanism for the acid-catalyzed hydrolysis of ethyl benzoate, PhCOOCH2CH3.

Question. (A true story.) The chemistry department custodian was cleaning the organic lab when an unmarked bottle fell off a shelf and smashed on the floor, leaving a puddle of volatile liquid. The custodian began to wipe up the puddle, but he was overcome with burning in his eyes and a feeling of having an electric drill thrust up his nose. He left the room and called the fire department, who used breathing equipment to go in and clean up the chemical. Three students were asked to identify the chemical quickly so that the custodian could be treated and chemical could be handled properly. The students took IR and NMR spectra, which follow. The UV spectrum showedat 220 nm(E= 16,000). The mass spectrometer was down, so no molecular weight was available. Determine the structure of this nasty compound, and show how your structure fits the spectra.

Show how you would synthesize the following compounds, starting with acetylene and any compounds containing no more than four carbon atoms.

(a)hex-1-yne

(b)hex-2-yne

(c)cis-hex-2-ene

(d)trans-hex-2-ene

(e)1,1-dibromohexane

(f)2,2-dibromohexane

(g)pentanal, CH3CH2CH2CH2CHO

(h)pentan-2-one, CH3-CO-CH 2CH2 CH3

(i) (+/)-3,4-dibromohexane

(j)meso-butan-2,3-diol

(k)2-methylhex-3-yn-2-ol

Question: Arrange each group of compounds in order of increasing basicity.

  1. CH3COO-,CICH2C00- , and PhO-
  2. sodium acetylide, sodium amide, and sodium acetate
  3. sodium benzoate, sodium ethoxide, and sodium phenoxide
  4. pyridine, sodium ethoxide, and sodium acetate

Grignard reagents add to carbonate esters as they add to other esters.

(a) Predict the major product of the following reaction.

(b) Show how you would synthesize 3-ethylpentan-3-ol using diethyl carbonate and ethyl bromide as your only organic reagents.

(c) Diethyl carbonate is a liquid reagent that is easy to handle. In contrast, phosgene is a highly toxic and corrosive gas. Show how you might use diethyl carbonate instead of phosgene to make Lexan庐. Also, show how you might use diethyl carbonate instead of methyl isocyanate to make Sevin庐 insecticide.
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