ACETALDEHYDES, KETONES AND CARBOXYLIC ACIDS

1. The reaction C6H5COCl + H2 Pd / BaSO4 C6H5CHO + HCl, is called

i) Rosenmund’s reaction iii) HVZ reaction
ii) Sandmeyer’s reaction iv) Cannizaro’s reaction
2. Clemmensen reduction of a ketone is carried out in the presence of which of the
following?
i) H2 and Pt as catalyst iii) Zn – Hg with HCl
ii) Glycol with KOH iv) LiAlH4
3. The weakest acid amongst the following is
i) ClCH2COOH iii) HCOOH
ii) FCH2CH2COOH iv) CH2ICOOH
4. The reaction
CH3CN Na-EtOH X HNO2 Y Tollen’s reagent Z, Z is
i) CH3CHO III) CH 3CH2NHOH
ii) CH3CH2COOH IV) CH3COOH
5. The reagent with which both acetaldehyde and acetone react is
i) I2/NaOH iii) Carbonic acid
ii) Fehling’s reaction iv) Tollen’s reagent
6. Which of the following reagents can be used to prepare ketone from acid chloride?
i) Grignard’s reagent iii) Dimethyl cadmium
ii) LiAlH4 iv) Cadmium chloride
7.
+CH3COOCOCH3 anhy AlCl3 X, X is

i) Phenyl acetate iii) Benzoic acid

ii) Acetophenone iv) Benzophenone
8. Aspirin is known as
i) Acetyl salicylic acid iii) Acetyl salicylate
ii) Phenyl salicylate iv) Methyl salicylic acid
9. Which of the following does not give brick red precipitate with Fehling’s solution?
i) Acetaldeyde iii) D glucose
ii) Formalin iv) Acetone
10. The most suitable reagent for the conversion of R–CH2–OH R–CHO is
i) CrO3 iii) KMnO4
ii) PCC iv) K 2Cr2O7
11. Give simple chemical tests to distinguish between the following pairs of compounds:
i) Pentan–2–one and Pentan–3–one
ii) Phenol and Benzoic acid
12. Arrange the following compounds in the increasing order of their reactivity in
nucleophilic addition reactions:
i) Ethanal, Propanal, Propanone, Butanone
ii) Benzaldehyde, p–Tolualdehyde, p–nitrobenzaldehyde, Acetophenone
13. Draw the structures of the following derivatives :
i) The 2,4–Dinitrophenylhydrazone of benzaldehyde
ii) Cyclopropanone oxime
14. Predict the products formed when cyclohexanecarbaldehyde reacts with the following
reagents: ( Give the reactions)
i) Semicarbazide and weak acid
ii) Excess ethanol and acid
15. Predict the products:
i) KMnO4.H2SO4
∆
ii) C–CH3
O + CH3CH2NH2 H+

16. Write the structures of compounds A, B and C in each of the following reactions:
i) C6H5Br Mg/dry ether A a) CO 2 B PCl5 C
+
b) H3O
ii) CH3CN a) SnCl2/HCl A dil NaOH B ∆ C
+
b) H3O
17. How will you convert ethanal into the following compounds:
i) But –2–enoic acid
ii) 2–hydxoxypropanoic acid
iii) Butan –1–ol
18. Write the reactions involved in the following reactions:
i) Wolff – Kishner reduction
ii) Etard reaction
iii) Cannizzaro reaction
19. Give reasons:
i) Aldehydes are more reactive than ketones towards nucleophilic reagents
ii) Electrophilic substitution in benzoic acid takes place at meta position
iii) Carboxylic acid is a stronger acid than phenol
20. What products will be formed on reaction of propanal with 2–methylpropanal in the
presence of NaOH? In each case, indicate which aldehyde acts as a nucleophile
and which as electrophile.
 21. A) How will you bring about the following conversions:
i) Benzaldehyde to Benzophenone
ii) Bromobenzene to 1–phenylethanol
iii) Benzaldehyde to α–Hydroxyphenylacetic acid
B) Give the mechanism of esterification of carboxylic acids
22. A) Give IUPAC names of the following:
i) H3C – CH2 – CH2 – CH2 – C – C6H5
O
ii) CH2CHO
Br

iii) HOOC – CH2 – COOH

B) i) Formic acid reduces Tollen’s reagent but acetic acid does not. Why?
ii) What is vinegar?
23. i) An organic compound (A) has characteristic odour. On treatment with NaOH, it
forms compounds (B) and(C). Compound (B) has molecular formula C 7H8O which
on oxidation gives back(A). The compound (C) is sodium salt of acid. When (C) is
treated with soda-lime, it yields an aromatic compound (D). Deduce the
structures of (A), (B), (C) and (D). Write the sequence of reactions involved.
ii) Describe the mechanism of the addition of Grignard reagent to the carbonyl
group of a compound to form an adduct which on hydrolysis yields an alcohol.