CHEMISTRY CLASSES 9868366053, 9968253763

Time: 2 hour ALDEHYDES, KETONES AND CARBOXYLIC ACIDS Max. Marks: 50

1. Write IUPAC name of the following compound:

OH

CI O (1)

2. Complete the following:

CH2 = CH CH CHO + NH2OH HCI

(1)
CH3
(1)
3. Why is benzoic acid stronger than ethanoic acid?
4. Write the IUPAC names of the following compounds:
CO2H
(i) CHO (ii) (CH3)2CH CH CH CH3
(1)
Br
5. Give Reason:
(i) NH2CONHNH2 has two NH2 groups but only one undergoes condensation with
carbonyI group of aldehydes or ketones.
(ii) Carboxylic acids have a higher boiling point than alcohols of comparable molecular
mass. (2)
6. Write the structures of A to D:
H2/Pd
(i) CH3COCI BaSO4
A dilute NaOH B
(ii) CH2CH3 KMnO4/KOH
C Br2/FeBr3
D
7. Explain the following name reactions:
Heat H+ (2)
(i) Wolff-Kishner reaction
(ii)
Hell-Volhard-Zelinsky reaction (2)
8. Complete the following by writing down the structure of the major product:

(i) CH3CH2MgBr + CHO H+/H2O

(ii)
(iii) (CH3)2CHMgBr + CO2 H2O/H+
9. Account for the following:
(2)
 CHEMISTRY CLASSES 9868366053, 9968253763

(i) 2, 4, 4-trimethyI cyclohexanone forms cyanohydrin with HCN but 2, 2, 6-trimethyI

cyclohexanone does not.
(ii) Propanone is more volatile than propanol. (2)
10. Explain the following name reactions:
(i) Aldol condensation
(2)
(ii) Cannizzaro reaction
11. Arrange the following in order of increasing property indicated:
(i) HCHO, CH3COCH3,CH3CH2CHO, C6H5CHO (towards HCN)
(ii) CICH2COOH, FCH2COOH, CH3COOH, C6H5COOH (acidic strength)
(iii) CH3CHO, CH3COCH3, CH3COOH, CH3OCH3 (boiling point) (3)
12. How will you bring about the following conversions?
(i) Ethanol to 2-hydroxypropanoic acid
(ii) Propanoic acid to propanal
(iii) Benzene to benzoic acid (3)
13. (a) Which of the following reagents are used to distinguish the following pair of organic
compounds?
(i) Methanal and methanoic acid
(ii) Acetophenone and benzophenone
(iii) Propanone and propanal
Reagents are: NaHCO3, I2/NaOH, [Ag (NH3)2] OH
(b) Write the structure of the following compound:
2-Hydroxy-5-oxo pentanoic acid
(C) Complete the following:
O

C CHO Conc. NaOH

(3)

14. (a) Covert:

(i) Methanal into n-butane
(ii) EthyI benzene into benzyI alcohol
(b) Why is benzoic acid a tronger acid than phenol? (3)
15. (i) Write the mechanism of the following reaction:
CH3 CHO + HCN OH- CH3 CH CN

OH

(ii) Write the structures of compounds A to C:

 CHEMISTRY CLASSES 9868366053, 9968253763

O
H2/Pd NH2NH2 KOH
CH3CH3 C CI A B Glycol
C (3)
BaSO4 HCI
16. How will you make the following conversions?
(i) Ethanoic acid into 2-methyI propan-2-ol
(ii) Ethanal into butane-1, 3-diol
(iii) Ethylbenzene into methyl benzoate (3)
17. Give a chemical test to distinguish between the following pair of organic compounds:
(i) Ethanal and propanal
(ii) Ethanoic acid and methanoic acid
(iii) Benzoic acid and phenol
(3)
18. (a) Give reason:
(i) Propanone is completely miscible in water in all proportions but acetophenone is
immiscible.
(ii) 2-MethyI benzoic acid is stronger acid than benzoic acid.
(b) Convert ethanol into 2-hydroxybutanal. (3)
19. (a) Organic compound A (C3H8O) gives a brisk effervescence with sodium metal. On
reaction with pyridinium chlorochromate, A forms B (C3H6O). Vigorous oxidation of B
gives acetic acid. B gives a yellow precipitate with 2,4-DNP and forms a compound C
with semicarbazide. Identify compounds A,B and C and write the reactions involved.
(b)(i) Draw the structure of the carbonyI group.
(ii) Predict the hybridization of the carbon atom.
(iii) Label the nucleophilic and the electrophilic centres.
(iv) What is the geometry of the carbonyI group? (3 + 2 = 5)
20. (a) Organic compound A (C8H16O2) on hydrolysis in acidic conditions gives a carboxylic
acid B and an alcohol C.
Dehydration of alcohol C gives but-1-ene. C on vigorous oxidation gives B.
(i) What are the structures of A, B and C?
(ii) Write IUPAC name of A.
(iii) What happens when A reacts with LiAIH4?
(b) What happens when (give chemical equation only)
(i) Ethanal reacts with excess of methanol in the presence of dry HCI gas
(ii) Acetone reacts with hydroxylamine in acidic medium.
(3 + 2 = 5)