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Concept explainers
(a)
Interpretation:
The increasing order of basicity of the given compounds is to be stated.
Concept Introduction:
Pyridine is a heterocyclic compound which contain nitrogen atom as heteroatom. The lone pair of nitrogen atom pyridine is not delocalized over the ring. Pyridine is basic in nature. The basicity of pyridine compounds changes with substitution. Basicity of pyridine compounds depends on the nucleophilicity of their nitrogen lone pair.
(b)
Interpretation:
The increasing order of basicity of the given compounds is to be stated.
Concept Introduction:
Pyridine is a heterocyclic compound which contain nitrogen atom as heteroatom. The lone pair of nitrogen atom pyridine is not delocalized over the ring. Pyridine is basic in nature. The basicity of pyridine compounds changes with substitution. Basicity of pyridine compounds depends on the nucleophilicity of their nitrogen lone pair.
(c)
Interpretation:
The increasing order of basicity of the given compounds is to be stated.
Concept Introduction:
The basicity of compounds can be compared by comparing the stability of their conjugate acid. If the conjugate acid formed is more stable than the basicity of compound will be greater. Resonance structure containing positive charge on electronegative atom is less stable.
(d)
Interpretation:
The increasing order of basicity of the given compounds is to be stated.
Concept Introduction:
The basicity of compounds can be compared by comparing the stability of their conjugate acid. If the conjugate acid formed is more stable than the basicity of compound will be greater. Resonance structure containing positive charge on electronegative atom is less stable.
(e)
Interpretation:
The increasing order of basicity of the given compounds is to be stated.
Concept Introduction:
The basicity of compounds can be compared by comparing the stability of their conjugate acid. If the conjugate acid formed is more stable than the basicity of compound will be greater. Resonance structure containing positive charge on electronegative atom is less stable.
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Chapter 26 Solutions
EBK ORGANIC CHEMISTRY
- Arrange each group of compounds in order of increasing acidity.(c) benzoic acid, o-nitrobenzoic acid, m-nitrobenzoic acidarrow_forwardArrange 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_forwardEach of the following is a much weaker base than aniline. Present a resonance argument to explain the effect of the substituent in each case. (a) o-Cyanoaniline (c) p-Aminoacetophenonearrow_forward
- Arrange each group of compounds in order of increasing acidity.(b) p-toluenesulfonic acid, acetic acid, chloroacetic acidarrow_forwardA carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons. (b) Compare the resonance forms with those given previously for an acid protonated on thecarbonyl oxygen atom.(c) Explain why the carbonyl oxygen atom of a carboxylic acid is more basic than thehydroxy oxygen.arrow_forward(c) Arrange the following compounds in order of increasing acidity, and explain the reasons fo your choice of order: phenol, cyclohexanol, 2-fluorocyclohexanol, 2-fluoronhenolarrow_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_forward(a) Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol. Give two reasons.(b) How will you bring about the following converstions?(i) Propanone to propane (ii) Benzoyl chloride to benzaldehyde(iii) Ethanal to but-2-enalarrow_forwardShow how you can synthesize the following compounds starting with benzene, toluene, and alcohols containing no morethan four carbon atoms as your organic starting materials. Assume that para is the major product (and separable fromortho) in ortho, para mixtures.(a) pentan-1-amine (b) N-methylbutan-1-aminearrow_forward
- 4. Each of the following is a much weaker base than aniline. Present a resonance argument to explain the effect of the substituent in each case. (a) o-cyanoaniline (b) C6H5NHCOCH3 (c) p-aminoacetophenonearrow_forwardRank the compounds in each of the following groups in order of their reactivity to electrophilic substitution: (a) Nitrobenzene, phenol, toluene, benzene (b) Phenol, benzene, chlorobenzene, benzoic acid (c) Benzene, bromobenzene, benzaldehyde, anilinearrow_forward(a) Explain why phentermine [PhCH2C(CH3)2NH2] can’t be made by a reductive amination reaction.(b) Give a systematic name for phentermine, one of the components of the banned diet drug fen–phen.arrow_forward
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