TEST- 1

Chapter - 12
Aldehydes, Ketones and Carboxylic Acids

M.M:- 50

➢ Answer the following questions ( 2 marks each)

Q-1 Give a possible explanation for each one of the following:

a. There are two – NH2 groups in semicarbazide. However, only one

such group is involved in the formation of semicarbazones.
b. Cyclohexanone forms cyanohydrins is good yield but 2,2,6-trimethyl
cyclohexanone does not.

Q-2 Explain the mechanism of a nucleophilic attack on the carbonyl group

of an aldehyde or a ketone.

Q-3 Write the reaction involved in the following:

a. Hell-volhard Zelinsky reaction

b. Decarboxylation reaction

Q-4 Although phenoxide ion has more number of resonating structure than
than carboxylate ion , carboxylic acid is stronger than phenol. Give two
reasons.

Q-5 Arrange the following compounds in increasing order of their property

as indicated:
a. Benzoic acid , 3,4-dinitrobenzoic acid, 4-methoxybenzoic acid ( acidic
strength)
b. CH3CH2CH(Br)COOH
CH3CH(Br)CH2COOH
(CH3)2CHCOOH ( acidic strength)

➢ Answer the following questions ( 3 marks each)

Q-1 Write the structures of the main products of the following reaction:

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Q-2 An organic compound A (Molecular formula = C8H16O2) was hydrolysed
with dilute sulphuric acid to give a carboxylic acid B and an alcohol C.
Oxidation of C with chromic acid also produced B. On dehydration C
gives but-1-ene. Write the reactions involved.

Q-3 How do you convert the following :

a. Benzaldehyde to 3-Phenylpropan-1-ol.
b. Benzaldehyde to α Hydroxyphenylacetk acid
c. Benzoic acid to m-Nitrobenzy 1 alcohol

Q-4 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.

Q-5 Write the structures of the following compounds:

a. α-Methoxypropionaldehyde
b. 3-Hydroxybutanal
c. 2-Hydroxycyclopentane carbaldehyde
➢ Answer the following questions ( 5 marks each)

Q-1 Complete each synthesis by giving missing starting material, reagent

or products.

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Q-2 (i) Acetaldehyde, Acetone, Di tert. butyl ketone, Methyl tert. butyl
ketone (reactivity towards HCN).
(ii) An alkene with molecular formula C5H10 on ozonolysis gives a
mixture of two compounds, B and C. Compound B gives positive
Fehling test and also reacts with iodine and NaOH solution.
Compound C does not give Fehling solution test but forms iodoform.
Identify the compounds A, B and C.

Q-3 (i) Write the product(s) in the following reactions

(ii) Give simple chemical tests to distinguish between the following pair
of compounds:
a. Butanal and Butan-2-one
b. Benzoic acid and phenol

Q-4 (i) Write the chemical reactions involved in Wolff-Kishner reduction.

(ii) Arrange the following in increasing order of their reactivity
towards nucleophilic addition reaction.
C6H5 COCH3 ,CH3 CHO, CH3COCH3
(iii) Why carboxylic acid does not give reactions of carbonyl group?
(iv) Write the product in the following reaction:
CH3CH2CH CH CH2CN (i) (t-but)2-AIH
(ii) H2O

(v) A and B are two functional isomers of compound C3H6O. On heating

with NaOH and I2 , isomers B forms yellow precipitate of iodoform
whereas isomer A does not form any precipitate. Write the formula
of A and B.

Q-5 An organic compound A on treatment with ethyl alcohol gives a

carboxylic acid B and compound C. Hydrolysis of C under acidified
conditions gives B and D. Oxidation of D with KMnO4 also gives B. B on
heating with Ca(OH)2 gives E having molecular formula C3H6O. E does
not give tollen’s test and doesnot reduce Fehling’s solution but forms a
2,4-dinitrophenylhydrazone. Identify A, B, C, D and E.

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