a) LiAlH4, then H3O+
Interpretation:
The product produced when p-methylbenzoic acid is treated with LiAlH4 and then with H3O+ is to be predicted.
Concept introduction:
To predict:
The product produced when p-methylbenzoic acid is treated with LiAlH4 and then with H3O+.
b) N-Bromosuccinimide in CCl4
Interpretation:
The product produced when p-methylbenzoic acid is treated with N-bromosuccinimide in CCl4 is to be predicted.
Concept introduction:
N-bromosuccinimide in CCl4 is used for introducing a Br in the benzyl carbon.
To predict:
The product produced when p-methylbenzoic acid is treated with N-bromosuccinimide in CCl4.
c) CH3MgBr in ether, then H3O+
Interpretation:
The product produced when p-methylbenzoic acid is treated with CH3MgBr and then with H3O+ is to be predicted.
Concept introduction:
Grignard reagents will react with the carboxyl hydrogen to yield
To predict:
The product produced when p-methylbenzoic acid is treated with CH3MgBr and then with H3O+.
d) KMnO4, H3O+
Interpretation:
The product produced when p-methylbenzoic acid is treated with KMnO4 in the presence of H3O+ is to be predicted.
Concept introduction:
When treated with KMnO4 in the presence of H3O+, the side chain in
To predict:
The product produced when p-methylbenzoic acid is treated with KMnO4 in the presence of H3O+.
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Chapter 20 Solutions
Organic Chemistry
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- (a) Draw the structures of the following compounds :(i) 4-Chloropentan-2-one (ii) p-Nitropropiophenone(b) Give tests to distinguish between the following pairs of compounds :(i) Ethanal and Propanal (ii) Phenol and Benzoic acid(iii) Benzaldehyde and Acetophenonearrow_forwardWrite a balanced chemical equation for each of the following reactions: (a) Phenol + sodium hydroxide (b) Product of part (a) + ethyl bromide (c) Product of part (a) + butyl p-toluenesulfonate (d) Product of part (a) + acetic anhydride (e) o-Cresol + benzoyl chloride (f) m-Cresol + ethylene oxide (g) 2,6-Dichlorophenol + bromine (h) p-Cresol + excess aqueous bromine (i) Isopropyl phenyl ether + excess hydrogen bromide + heatarrow_forwardSuggest readily available starting materials and reaction conditions suitable for obtaining each of the following compounds by a procedure involving alkylation of nucleophilic carbon. (a) PHCH2CH2CHPH (b) (CH3)½C=CHCH2CH2CCH2CO;CH3 ČN (c) (d) CH2=CHCH=CHCH2CH2CO,H CH3 CH2CO2H CH3 CH3CO CH;CH2CH2 (f) (e) 2,3-diphenylpropanoic acid (g) CH3Oʻ CH3CH2 CH2CH=CH2arrow_forward
- Predict the products of the following reactions.(a) cyclohexylmethanol + TsCl/pyridine (b) product of (a) + LiAlH4arrow_forwardPredict the major products of the following reactions: (a) Nitration of bromobenzene (b) Bromination of nitrobenzene (c) Chlorination of phenol (d) Bromination of anilinearrow_forwardWrite structural formulas for the cyclohexadienyl cations formed from aniline (C6H5NH2) during(a) Ortho bromination (four resonance structures)(b) Meta bromination (three resonance structures)(c) Para bromination (four resonance structures)arrow_forward
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