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Concept explainers
(a)
Interpretation:
The amine among
Concept introduction:
Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic
Staudinger reaction is also used to prepare primary amines. In this reaction,
(b)
Interpretation:
The synthesis of
Concept introduction:
Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.
(c)
Interpretation:
The synthesis of
Concept introduction:
Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.
(d)
Interpretation:
The reason as to why,
Concept introduction:
Gabriel synthesis is a reaction in which a primary amine is formed when a phthalimide anion is alkylated and then undergoes hydrolysis. It is the best method to prepare primary aliphatic amines. Aromatic amines cannot be prepared by this reaction.
Staudinger reaction is also used to prepare primary amines. In this reaction, alkyl halides react with azide to form alkyl azides which on reaction with triphenylphosphine form an intermediate, phosphazide. The phosphazide undergoes rearrangement to form iminophosphorane which on hydrolysis yield primary amines.
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Chapter 23 Solutions
EBK ORGANIC CHEMISTRY
- (D)The best route to synthesise aromatic primary amines is by reduction of the corresponding nitro compounds. Draw the reaction scheme for the preparation of p-toluidine.arrow_forwardPredict the products from the reactions of the following amines with sodium nitrite indilute HCl.(a) cyclohexanaminearrow_forwardShow how to prepare the following aromatic amines by aromatic nitration, followed by reduction. You may use benzene andtoluene as your aromatic starting materials. (c) m-bromoaniline (d) m-aminobenzoic acidarrow_forward
- Show how to synthesize the following amines from the indicated starting materials.(a) N-cyclopentylaniline from anilinearrow_forwardShow how to synthesize the following amines from the indicated starting materials byreductive amination.(a) benzylmethylamine from benzaldehydearrow_forwardThe –NHCOR group of an amide is an activating group, but it is not as strongly activating as NH2. (a) Explain why it is an activating group. (b) Explain why it is less activating than NH2.arrow_forward
- Arrange the members of each group in order of decreasing basicity: (a) Ammonia, aniline, methylamine (b) Acetanilide, aniline, N-methylaniline (c) 2,4-Dichloroaniline, 2,4-dimethylaniline, 2,4-dinitroaniline (d) 3,4-Dichloroaniline, 4-chloro-2-nitroaniline, 4-chloro-3-nitroaniline (e) Dimethylamine, diphenylamine, N-methylanilinearrow_forwardShow how to prepare the following aromatic amines by aromatic nitration, followed by reduction. You may use benzene andtoluene as your aromatic starting materials. c) m-bromoanilinearrow_forwarda) What are the difficulties with the following reaction to synthesize an amine. + HBr Br + NH3 NH2 b) Show a possible alternatives to this synthesis.arrow_forward
- Phenylacetone can form two different enols.(a) Show the structures of these enols.(b) Predict which enol will be present in the larger concentration at equilibrium.(c) Propose mechanisms for the formation of the two enols in acid and in basearrow_forwardShow how Gabriel syntheses are used to prepare the following amines.(a) benzylaminearrow_forwardAliphatic amines are more basic than ammonia, whereas aromatic amines are less basic than ammonia. Is that true or false?arrow_forward
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