Problem 2
Name the following compounds according to IUPAC system of nomenclature: (i) \(\mathrm{CH}_{3} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CHO}\) (ii) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COCH}\left(\mathrm{C}_{2} \mathrm{H}_{5}\right) \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Cl}\) (iii) \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCHO}\) (iv) \(\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{COCH}_{3}\) (v) \(\mathrm{CH}_{3} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{CH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{COCH}_{3}\) (vi) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}_{2} \mathrm{COOH}\) (vii) \(\mathrm{OHCC}_{6} \mathrm{H}_{4}\) CHO \(-p\)
Problem 3
Draw the structures of the following compounds. (i) 3 -Methylbutanal (ii) \(p\) -Nitropropiophenone (iii) \(p\) -Methylbenzaldehyde (iv) 4 -Methylpent-3-en-2-one (v) 4-Chloropentan-2-one (vi) 3 -Bromo-4-phenylpentanoic acid (vii) \(p, p^{\prime}-\) Dihydroxybenzophenone (viii) Hex-2-en-4-ynoic acid
Problem 4
Write the IUPAC names of the following ketones and aldehydes. Wherever
possible, give also common names.
(i) \(\mathrm{CH}_{3} \mathrm{CO}\left(\mathrm{CH}_{2}\right)_{4}
\mathrm{CH}_{3}\)
(ii) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CHBrCH}_{2}
\mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{CHO}\)
(iii) \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{5} \mathrm{CHO}\)
(iv) \(\mathrm{Ph}-\mathrm{CH}=\mathrm{CH}-\mathrm{CHO}\)
(v)
Problem 5
Draw structures of the following derivatives. (i) The \(2.4\) -dinitrophenylhydrazone of benzaldehyde (ii) Cyclopropanone oxime (iii) Acetaldehydedimethylacetal (iv) The semicarbazone of cyclobutanone (v) The ethylene ketal of hexan-3-one (vi) The methyl hemiacetal of formaldehyde
Problem 6
Predict the products formed when cyclohexanecarbaldehyde reacts with following reagents. (i) PhMgBr and then \(\mathrm{H}_{3} \mathrm{O}^{+}\) (ii) Tollens' reagent (iii) Semicarbazide and weak acid (iv) Excess ethanol and acid (v) Zinc amalgam and dilute hydrochloric acid
Problem 7
Which of the following compounds would undergo aldol condensation, which the Cannizzaro reaction and which neither? Write the structures of the expected products of aldol condensation and Cannizzaro reaction. (i) Methanal (ii) 2-Methylpentanal (iii) Benzaldehyde (iv) Benzophenone (v) Cyclohexanone (vi) 1 -Phenylpropanone (vii) Phenylacetaldehyde (viii) Butan-1-ol (ix) 2,2-Dimethylbutanal
Problem 8
How will you convert ethanal into the following compounds? (i) Butane-1,3-diol (ii) But-2-enal (iii) But-2-enoic acid
Problem 9
Write structural formulas and names of four possible aldol condensation products from propanal and butanal. In each case, indicate which aldehyde acts as nucleophile and which as electrophile.
Problem 10
An organic compound with the molecular formula \(\mathrm{C}_{3} \mathrm{H}_{10} \mathrm{O}\) forms \(2.4\) -DNP derivative, reduces Tollens" reagent and undergoes Cannizzaro reaction. On vigorous oxidation, it gives \(1.2\) -benzenedicarboxylic acid. Identify the compound.
Problem 12
Arrange the following compounds in increasing order of their property as indicated: (i) Acetaldehyde. Acetone, Di-tert-butyl ketone, Methyl tert-butyl ketone (reactivity towards HCN) (ii) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}(\mathrm{Br}) \mathrm{COOH}, \mathrm{CH}_{3} \mathrm{CH}(\mathrm{Br}) \mathrm{CH}_{2} \mathrm{COOH} .\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCOOH}\). \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{COOH}\) (acid strength) (iii) Benzoic acid. 4-Nitrobenzoic acid, 3.4-Dinitrobenzoic acid. 4-Methoxybenzoic acid (acid strength)
