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

(a)

(b)

(c)

Short Answer

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(a)

(b)

(c)

Step by step solution

01

Amines and carboxylic acids

Amines are compounds containing the -NH2group and carboxylic compounds with the –COOH 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: Show the products you expect when each compound reacts with NBS with light shining on the reaction.

b)

The 2000 Nobel Prize in Chemistry was awarded for work on polyacetylenes. Acetylene can be polymerized using a Ziegler-Natta catalyst. The cis or trans stereochemistry of the products can be controlled by careful selection and preparation of the catalyst. The resulting polyacetylene is an electrical semiconductor with a metallic appearance. cis-Polyacetylene has a copper color, and trans-polyacetylene is silver.

(a) Draw the structures of cis- and trans-polyacetylene.

(b) Use your structures to show why these polymers conduct electricity.

(c) It is possible to prepare polyacetylene films whose electrical conductivity is anisotropic. That is, the conductivity is higher in some directions than in others. Explain how this unusual behavior is possible.

Show how you would synthesize any of the standard amino acids from each starting material. You may use any necessary reagents.

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

(a) isopentyl alcohol isopentyl acetate (banana oil)

(b) 3-ethylpentanoic acid3-ethylpentanenitrile

(c) isobutylamineN-isobutylformamide

(d) ethyl acetate3-methylpentan-3-ol

(e) cyclohexylamineN-cyclohexylacetamide

(f) bromocyclohexanedicyclohexylmethano

(g)

(h)

(a) Propose a mechanism for the following reaction:

(b) Use the bond-dissociation enthalpies given in Table 4-2 (page 203) to calculate the value of ∆H° for each step shown in your mechanism. (The BDE for is about 280 kJ/mol, or 67 kcal/mol.) Calculate the overall value of ∆H° for the reaction. Are these values consistent with a rapid free-radical chain reaction?

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