SAMPLE PAPER (2022-23)
CHEMISTRY THEORY (043)
MARKING SCHEME
CHAPTER -ALDEHYDE KETONE AND CARBOXYLIC ACID
SECTION A
Q1 to 18 each correct answer 1 mark
1. (a) benzyl alcohol + sodium formate
Explanation: When a mixture of formaldehyde and another aldehyde without an α-hydrogen
atom is treated with concentrated alkali, it oxidizes formaldehyde to carboxylic acid and reduces
another aldehyde to alcohol.
2. (d) Tollen's reagent
Explanation: Formic acid has an aldehyde group. It reduces Tollen's reagent to a silver mirror-like
other aldehydes. Tollen's test is not given by Carboxylic acids.
3. (b) C6H5COCH3
Explanation: Compared with aliphatic ketones, aromatic ketones are less reactive than
aldehydes. The reaction between acetophenone and NaHSO3 is therefore not initiated.
4. (c) Aldol
Explanation: Aldol is obtained by heating acetaldehyde molecules with dilute NaOH solutions.
5. (a) hexane-2,4-dione
6. (b) nucleophilic addition
7. (b)
Explanation: Ketones are formed when secondary alcohols are oxidised and dehydrogenated.
Aldehydes are produced by the same processes with primary alcohols.
8. ( b) Benzoic acid
9. (c) Formaldehyde
10. (a) But-2-enal.
11. (c) boiling ethyne with water in the presence of HgSO 4 and H2SO4
12. (c) propanal and methanal
13. (c) C6H5CHO
14. (b) 2 and 5 only
15. (a)
16. (b)
17. (c)
18. (d)
SECTION B
19. In fluoroacetic acid, Fluorine being electron withdrawing group stabilizes the conjugate base
through delocalization of the negative charge
Therefore fluoroacetic acid is a stronger acid than acetic acid. 2
20. Carboxylic acids have more extensive association of molecules through intermolecular hydrogen
bonding than alcohols. Moreover their boiling points are higher than alcohols of same carbon
atoms. 2
Ethanoic acid exists as dimer in vapour state in which two molecules remain together by
hydrogen bonding. This increases the effective molecular mass to 120.
21. (a) When Propanone is treated with methylmagnesium iodide and then hydrolysed, tertiary
butyl alcohol is formed 1
(b) When Benzene is treated with in presence of anhydrous , acetophenone
is formed 1
OR
(a) Butanone is treated with methylmagnesium bromide and then hydrolysed, and 1
(b) Sodium benzoate is heated with soda lime ? 1
22. (i) The order of electron withdrawing ability is- 1
−NO2>F−>−H>−CH3
Therefore, the order of acidic character is-
O2N−CH2COOH>F−CH2COOH>HCOOH>CH3COOH
(ii) Addition of HCN is a nucleophilic addition reaction.
The +I effect is more in ketone than in aldehyde. Thus ketone will be least reactive in nucleophilic
addition reactions. The presence of electron withdrawing group increases the reactivity towards the
addition of HCN while the presence of electron donating group decreases the reactivity of compound
towards nucleophilic addition reaction.
Benzaldehyde does not favour nucleophilic addition reaction due to resonance stabilisation.
Hence the increasing order of reactivity towards the addition of HCN will be-
Acetophenone < Benzaldehyde < Acetone < Acetaldehyde 1
23.
1
24.
(i) In benzoic acid, the -COOH group is attached to sp2- carbon (more electronegative)while in acetic
acid -COOH group is attached to sp3- carbon(less electronegative) 1
(ii) It is due to steric and electronic reasons. Presence of methyl group in
ethanal, hinders the approach of nucleophile to carbon of and it
also reduces the electrophilicity of the carbonyl gp. due to effect.
1
25. Propanal and propanone : 2
Propanal gives silver mirror test with Tollen's reagent. Propanone does not gives this test.
Propanal gives red ppt with Fehlings solution but propanone does not give this test.
SECTION C
26. (i) When propanal reacts with excess of methanol in the presence of HCl, it forms 1,1-dimethoxy propane.
1
(ii) Propanal having α-hydrogen atom undergo aldol condensation in presence of dil. NaOH and forms 3-hydroxy-
2-methyl pentanal. 1
(iii) The carbonyl group of propanal is reduced to CH2 group on treatment with hydrazine followed by heating
with KOH in ethylene glycol and the product formed will be propane. 1
27. 1+1+1
28. 1+1+1
29. a) Wolff kishner reduction is a chemical name reaction in which aldehydes and ketones are
converted into an alkane in presence of hydrazine, base and thermal conditions. When aldehydes or
ketones are heated with hydrazine and potassium hydroxide in ethylene glycol, it results in the
formation of alkanes.
Let us see the chemical reaction:
(b) As we know that, aldehydes are more reactive than alcohol because aldehydes are less hindered
than ketones. Aliphatic ketones are more reactive than aromatic ketones because aromatic ketoses
have delocalisation of electrons. Therefore the reactivity order can be written as:
𝐂𝟔𝐇𝟓𝐂𝐎𝐂𝐇𝟑, < 𝐂𝐇𝟑𝐂𝐎𝐂𝐇𝟑, <𝐂𝐇𝟑 – 𝐂𝐇𝐎 1
(c)Carboxylic acids do not give reactions to carbonyl groups because the lone pair of electrons on oxygen
atoms of the −OH−OH group of carboxylic acid is less electrophilic than the carbonyl group of ketones
and aldehydes. 1
(d) Let us write the product of the given reaction: 1
(e) B is a methyl ketone as it forms yellow precipitate of iodoform, that means it undergoes a haloform
reaction. hence, B is acetone CH3COCH3 . The isomer A does not form any precipitate, therefore it will
not have any methyl ketone. Hence isomer A is propanal CH3CH2CHO 1
30. 1+1+1
OR
i. Pentan-2-one and Pentan -3 -one Pentan – 2-one contains CH3CO group and as such it will give iodo-
form test with NaOI [NaOH + I2] while no such group is there in pentan -3- one and so it will not give
iodoform test. 1
ii. Benzaldehyde and Acetophenone Benzaldehyde is an aromatic aldehyde while acetophenone is a
methyl ketone. These may be distinguished as follows. 1
(a) Iodoform test: Acetophenone, due to the presence of CH3CO group, will give iodoform test with NaOI
(NaOH +I2), while benzaldehyde will not give this test.
(b) Silver mirror test: Benzaldehyde, being an aromatic aldehyde, will reduce tollens’ reagent to silver.
On other hand acetophenone, a ketone will not give this test.
iii. Ethanal and Propanal: As ethanal contains CH3CO group it will give iodoform test with NaOH and I2.
On the other hand propanal will not give this test. 1
SECTION D
31.
Ans (i) (a): It is an example of cross Cannizzaro reaction where aromatic aldehyde gets reduced
to alcohol and aliphatic aldehyde gets oxidised to its sodium salt (both aldehydes must not
contain any α-hydrogen). 1
(ii) (c) C6H5CHO 1
(iii) (a): The Cannizzaro product of given reaction yields 2, 2, 2-trichloroethanol. 2
OR
No , as it is a bimolecular redox reaction.
32.
(i)Answer:(c) Hydrolysis 1
(ii) Answer:(b) 1
(iii) Acetophenone and Formaldehyde 2
OR
Answer- The Carbonyl compound having α-hydrogen undergoes an aldol condensation reaction.
SECTION E
33. 2+2+1
(a) Since, the compound (A) gives a positive iodoform test but negative Tollen's test, so it must be a
methyl ketone. From the given molecular formula C5H10O(A) can be 2-pentanone
(b)
(i)
(ii)
(c) Distinction between acetaldehyde and benzaldehyde : - Acetaldehyde and benzaldehyde can be
distinguish by Fehling solution. Acetaldehyde gives red coloured precipitate with Fehling solution
while benzaldehyde does not.
OR
(a)
(b)
4–hydroxy–3–methoxy-benzaldehyde
(c)
34. 2+2+1
(a)
(b)
(c) In a carbonyl group, the oxygen is extremely electronegative and it attracts the electron cloud
towards itself developing a partial positive charge on the α-carbon. To reduce the positive charge, α-
carbon looses its hydrogen readily and makes it acidic in nature.
OR
(d)
(e)
It is because —OH has more —I effect than —OCH3 group.
OR
3+2
(b)
(i) Aromatic carboxylic acids do not undergo Friedel-Crafts reaction as the carboxyl (−COOH) group is
deactivating and Lewis acid catalyst AlCl3 gets bonded to the carboxyl group. The carboxyl (−COOH)
group withdraws electron density from benzene ring through inductive and resonance effects.
(ii) pKa value of 4-nitrobenzoic acid (3.41) is lower than that of benzoic acid (4.19). Lower is the pKa
value, greater is the acid strength. The electron withdrawing nitro (−NO2) group increases the acidity of
benzoic acid.
35. 2+3
(i)
(ii)
(b)
(A)
B= Positive Fenling - aldehyde group
= Positive Iodoform test
C - negative testing
= positive Iodoform
=
OR
(a) 2+3
(i)
Step-1:—Conversion of benzoic acid to benzamde.
Benzoic acid is treated with thionyl chloride to form benzoyl chloride,which on further treatment with
ammonia gives benzamide.
Step-2:—Conversion of benzamide to aniline.
Benzamide is subjected to Hoffmann bromamde degradation by reacting with Br₂ and NaOH to form
aniline.
(ii)
