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VIJETA – 2023 Class 12th One-shot Series

Aldehyde Ketone and Carboxylic Acid Practice Sheet

1. Arrange the following compounds in increasing 10. How will you bring about the following
order of their property as indicated in bracker. conversions?
(i) Propanone to propane
(ii) Benzoyl chloride to benzaldehyde.
(iii) Ethanal to but-2-enal.

11. Write the structures of the main products of

2. Write the structure of p-methylbenzaldehyde. following reactions:

3. Write the IUPAC name of the following compound: (i)

(ii)

4. Write the IUPAC name of the following compound: (iii)

12. (i) Describe the mechanism of the addition of

5. Write the structure of 4-chloropentan-2-one.
6. Rearrange the following compounds in the
increasing order of their boiling points.
7. Give simple tests to distinguish between the
following pair of compounds:
Pentan-2-one and pentan-3-one.
8. Write the reactions involved in the following
reactions:
(i) Clemmensen reduction
(ii) Cannizzaro reaction
9. Explain the mechanism of a nucleophilic attack on
the carbonyl group of an aldehyde or a ketone.
Grinard’s reagent to the carbonyl group of a
compound to form an adduct which on
hydrolysis yield an alcohol.
(ii) Draw the structure of the following
compounds:
(a) 3-methylbutanal
(b) p-nitropropiophenone
13. (i) Write the products formed when benzaldehyde
reacts with the following reagents:
(a) CH3CHO in presence of dilute NaOH
(b) H2N—NH
(c) Conc. NaOH
(ii) Distinguish between following:
CH3—CH = CH—CO—CH3 and
CH3—CH2—CO—CH = CH2
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14. (i) Write the final products in the following: 21. Give reasons :
(a) (i) chloroacetic acid is stronger than acetic acid.
(ii) pH of reaction should be carefully controlled
15. Draw the structure of the following compound: while preparing ammonia derivatives of
Hexane-1, 6-dioic acid. carbonyl compounds..
22. Give simple chemical tests to distinguish between
16. Write IUPAC name of the following pairs of compounds:
(i) Ethanal and propanal.
(ii) Benzoic acid and phenol.

23. Give chemical tests to distinguish between the

following pairs of compounds:
17. Arrange the following compounds in increasing (i) Propanal and propanone.
order of their property as indicated in bracket. (ii) Benzaldehyde and benzoic acid.
(i) CCl3—COOH, CF3—COOH,
24. Write the structures of the main products in the
(CH 3 )3 C—COOH following reactions :.
(Acid strength)

(ii) (i)

18. How are the following conversions carried out? (ii)

(i) Ethyl cyanide to ethanoic acid
(ii) Butan-1-ol to butanoic acid
(iii) Benzoic acid to m-bromobenzoic acid
(iii)
19. An organic compound A (molecular formula
C8H16O2) was hydrolysed with dilute sulphuric acid
to give a carboxylic acid B and an alcohol C. 25. A compound A(C2H6O) on oxidation by PCC gave
Oxidation of C with chromic acid also produced B. B, which on treatment with aqueous alkali and
On dehydration C gives but-1-ene. subsequent heating furnished C. B on oxidation by
Write the equations for the reactions involved. KMnO4, forms a monobasic carboxylic acid with
molar mass 60 g mol–1. Deduce the structures of A,
B and C.
20. Name the reagents used in the following reactions.
(i) CH 3 — CO — CH 3 
?
 26. (i) Carry out the following conversions :
(a) p-nitrotoluene to 2-bromobenzoic acid
CH 3 — CO — CH 3 (b) Propanoic acid to acetic acid
|
(ii) An alkene with molecular formula C5H10 on
OH ozonolysis gives a mixture of two compounds,
B and C. Compound B gives positive Fehling
C6 H5  CH 2  CH3 
?

(ii) test and also reacts with iodine and NaOH
C6 H5  COO  K  solution.
Compound C does not give Fehling solution
test but forms iodoform. Identify the
compounds A, B and C.
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Hints & Solutions

1. The given aldehyde and ketones undergo 7. Propane-2-one and pentan-3-one can be
nucleophilic addition which HCN. In such case more distinguished by iodoform test.
the + I effect of alkyl group, more the steric hindrance On heating with NaOH + I2 or [NaOI], propan-2-one
and lesser will the reactivity, so, their increasing being a methyl ketone forms yellow ppt. of iodoform,
order will be whereas pentan-3-one does not.

2.

8. (i) Clemmensen reduction: The carbonyl group of

aldehydes and ketones is reduced to —CH2
group on treatment with zinc-amalgam and
concentrated hydrochloric acid. This reaction is
known as Clemmensen reduction

3.

(ii) Cannizzaro reaction: Aldehydes which do not

have -H atoms undergo self oxidation and
reduction reaction on treatment with conc.
4. Alkali. This reaction is known as Cannizzaro
reaction.
In this reaction, one molecule of aldehyde is
reduced to alcohol, while another molecule is
oxidized to salt of carboxylic acid.
5.

6. Boiling point is related to attractive forces. Stronger

the attractive force, higher is the boiling point.
Ethanol, i.e. CH3—CH2—OH undergoes extensive
intermolecular hydrogen bonding, therefore, its
boiling point is highest among all the given
compounds. In contrast, among CH3—CHO and
CH3—CH2—CH3, CH3CHO possess higher boiling
point than CH3CH2CH3 because CH3CHO possess
dipole-dipole interactions which are stronger than
van der Waals’ forces of attractioin existing in
CH3CH2CH3. Hence, the order of their increasing
boiling points is:
CH3—CH2—CH3 < CH3—CHO < CH3—CH2—OH
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9. Mechanism of a nucleophilic attack on carbonyl Benzophenone

carbon: A nucleophile attacks the electrophilic
carbon atom of the polar carbonyl group from a
(ii) H 3 C  C  C H  H 2 O 
Dil.H 2SO 4

direction approximately perpendicular to the plane of HgSO 4

sp2-hybridised orbitals of carbonyl carbon.

The hybridization of carbon changes from sp2 to sp3
and a tetrahedral intermediate is produced.
This intermediate immediately accepts a proton from
the reaction medium to give electrically neutral
product.
(iii)

p-nitrobenzaldehyde

10. (i) Conversion of propanone to propane 12. (i) Alcohols are produced by the addition reaction of
Grignard’s reagents with the carbonyl group of
aldehydes and ketones.
Mechanism
Step I: The first step of the reaction is the
nucleophilic addition of Grignards reagent to the
(ii) Conversion of benzoyl chloride to carbonyl group to from an adduct.
benzaldehyde

Step II: Hydrolysis of the adduct yields an alcohol.

(iii) Conversion of ethanol to but-2-enal

(ii) (a) 3-methylbutanal

11. (i) Friedel-Crafts reaction (acylation), i.e.

introduction of acyl group in benzene ring. (b) p-nitropropiophenone
(ii) Hydration of propyne, i.e. addition of water to
propyne and tautomerisation.
(iii) Etard’s reaction (aldehyde is formed, i.e. – CH3
group is converted into – CHO group).

(i)
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Hence, the order of nucleophilic addition:

C6H5COCH3 < CH3COCH3 < CH3CHO <
HCHO
13. (i) (a)
(iii)

(b) 15. Hexane – 1, 6 – dioic acid

HOOC — (CH2)4 — COOH

16. Note Naming will be done in alphabetical manner.

(c)

17. (i) More the electronegative halogen atom, greater

the stablisation and greater will be the acidic
(ii) Iodoform test is used to distinguish CH3 – strength. So,CCl3 —COOH < CF3COOH
Co – group containing compound from other. Also, with the increase in electron donating
O group, (alkyl group), acidity decreases.
|| Hence, the overall acidic strength of given
CH 3  CH  CH  C  CH 3  4NaOH  3I 2 compounds is
 CF3COOH > CC13COOH > (CH3)3CCOOH
CHI3 + H3C – CH = CH – COO–Na+ + 3NaI + (1)
(Yellow ppt) H2O (ii) Since, electron-donating groups decrease the
O acidic strength and electron-withdrawing groups
|| increase the acidic strength, therefore, 4-
CH3  CH 2  C  CH  CH 2  4NaOH  3I 2
methoxybenzoic acid is weaker acid and both 4-
 nitrobenzoic.acid and 2,4-dinitrobenzoic acid
No reaction are stronger acid than benzoic acid.
Moreover, the presence of an extra —NO2
groups in 2, 4-dinitrobenzoic acid increases
14. (i) (a) acidic strength than 4-nitrobenzoic acid.
Hence, the overall acidic strength order will be :

(b)

 a  DIBAL  H
(c) CH2  CH  CH2  CN  b  H O

3

CH2 = CH – CHO
(ii) As the number and size of the substituted group
increases, the hinderance to the attack of
nucleophile also increases.
Nucleophilic attack is difficult, when number of
attached group increases.
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21. (i) Cl is an electron withdrawing group, thus,

18.
increases the acidity of carboxylic acid by
stabilising the conjugate base through
delocalisation of the negative charge by
inductive effect. While in acetic acid no such
group is present which stabilises the conjugate
base.
That's why, chloroacetic acid because of the
 i  K 2Cr2O7
(ii) CH 3CH 2CH 2CH 2OH 
 ii  Dil . H 2 SO4
 presence of electron withdrawing group is more
Butanol
acidic than acetic acid (where no such group is
CH 3CH 2CH 2COOH
Butanoic acid present).
(ii) If the medium is too acidic, the ammo™
derivatives being basic in nature will form
respective ammonium salts. Due to the absence
(iii) of lone pair of electrons on the nitrogen atom,
these ammonium salt will no longer be
nucleophilic and hence, the reaction will not
occur.
However, if the medium is slightly acidic, the
19. (i) Ester produces a carboxylic acid and alcohol on protonation of the carbonyl group will not occur. This
hydrolysis. in turn will not increase the electron deficiency (or +
(ii) Ester A has 8 carbon atoms, calculate number ve charge) on the carbon atom of the carbonyl group
of C atoms in acid and alcohol. and hence, weak nucleophiles like ammonia
(iii) Guess the alcohol and acid according to the derivatives will not be able to react. Hence, the
given reactions. reaction will not occur. Therefore, to carry out such
(iv) Now guess the ester. reactions, an optimum value of pH is needed. Hence,
(v) Write all the related equations. pH should be controlled in such reactions.
Compound C on dehydration gives but-l-ene 22. (i) Iodoform test Given by CH3CO —
(CH3CH2H = CH2), so it must be butan-l-ol. When (ii) Sodium bicarbonate test Given by — COOH
subjected to oxidation C gives butanoic acid B. Thus, group containing compounds.
compound A is (i) Distinguishing test between ethanal and
CH3CH2CH2COOCH2CH2CH2CH3. propanal
The reactions involved are as follows: Iodoform test Ethanal because of the presence
H O/H + of CH3CO— skeleton gives positive iodoform
CH 3CH 2 CH 2 COOCH 2 CH 2 CH 2 CH 3 
2 
A
test whereas propanal due to the absence of
such a skeleton does not gives such test.
CH3CH 2 CH 2 COOH + CH 3CH 2CH 2CH 2OH
 B C  23. Name the different reagents needed to perform the
CH 3CH 2 CH 2 OH 
 CH 3CH 2 CH 2 COOH
CrO3 following reactions:
C   B (i) Phenol to benzene
(ii) Dehydration of propan-2-ol to propene.
CH 3CH 2 CH 2 CH 2 OH 
Conc.
H SO
 CH 3CH 2CH = CH 2 (iii) Friedel-Crafts acetylation of anisole.
2 4
C But-1-ene
(iv) Dehydrogenation of ethanol to ethanol.

O OH
20. (i) |
||
CH 3  C  CH 3   CH 3  CH  CH 3
NaBH 4

KMnO 4  KOH
(ii) C 6 H 5  CH 2  CH 3 

C6 H 5  COO  K 
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24. (i) 26. (i) (a) p-nitrotoluene to 2-bromobenzoic acid

(ii)

(iii)

25. Monobasic carboxylic acid = RCOOH. Given that,

molar mass of RCOOH = 60 g mol–1
(b) Propanoic acid to acetic acid
i.e. x + 12 + 16 + 16 + 1 = 60; x = 15
Step I CH3CH2 — COOH + NaOH

 CH 3CH 2 COONa+H 2O
Thus, R = — CH3 (molar mass 15) and the acid is
CH3COOH. Since, the acid is obtained by the Step II CH3 — CH2 — COONa
oxidation of aldehyde, so B is an aldehyde, i.e. 
NaOH+ CaO
C 2 H 6 + Na 2 CO 3
CH3CHO and A is CH3CH2OH as it gives B on
Step III C 2 H 6   CH 3COOH
K Cr O
oxidation by PCC. C is an alkene as it is formed by 2 2 7
 Oxidation 
subsequent heating of aldehyde (B) with aqueous  Aceticacid 
alkali. Thus, the involved reactions are as follows: (ii) Given alkene = C5H10, which on ozonolysis
gives (B) which gives positive Fehling test,
O means last carbon is bonded with double bond
||
CH 3  CH 2  OH 
PCC
 CH 3  C  H with next C-atom.
A  B Also, compound (B) reacts with iodine and NaOH,
means it has —CH3 group bonded with —CO-group.
O Thus structure of alkene is
||

4 KMnO
CH 3  C  OH
H 3C  C  C  CH 3
 –1 
| |
 Molecular weight,60g mol 
  CH 3 H

O OH O
|| | ||
OH –
2CH 3  C  H 
Aldol
 CH 3  CH  CH 2  CH
 B condensation
CH 3  C  O  O  C  CH 3
O | |
|| CH 3 H
C  B

Heat
 CH CH  CH  C H  Acetaldehyde 
–H O 2 3  Acetone 
C

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