ALDEHYDES, KETONES AND CARBOXYLIC ACIDS

Multiple Choice Questions:

1. Which of the following is most reactive in the nucleophilic addition reaction?
(A) HCHO
(B) CH3CHO
(C) CH3COCH3
(D) CH3COC2H5
2. Which of the following does not give aldol condensation reaction?
(A) CH3CHO

(B)

(C)

(D) CH3COCH3
3. What would be the major product of the given reaction?

(A) Ethanal
(B) Propanol
(C) Ethanol
(D) Propanal
4. Pentan-2-one and Pentan-3-one can be distinguished by:
(A) Fehling’s test
(B) Sodium bicarbonate test
(C) Tollens’ test
(D) Iodoform test
5.

This reaction is known as:

(A) Aldol condensation
(B) Cross-Aldol condensation
(C) Cannizzaro’s reaction
(D) Friedel-Crafts reaction
6. The product formed in the reaction:

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 (A)

(B)

(C)

(D)

7.

This reaction is known as:

(A) Cannizzaro’s reaction
(B) Etard reaction
(C) Rosenmund reduction
(D) Aldol condensation
8. Which of the following is an ‘Acetal’?

(A)

(B)

(C)

(D)

9. What is IUPAC name of the ketone A, which undergoes iodoform reaction to give
CH3CH=C(CH3)COONa and yellow precipitate of CHI3?
(A) 3−Methylpent−3−en−2−one
(B) 3−Methylbut−2−en−one
(C) 2, 3−Dimethylethanone
(D) 3−Methylpent−4−one
10. Acetic acid reacts with PCl5 to give:
(A) Cl−CH2−COCl
(B) Cl−CH2−COOH
(C) CH3−COCl
(D) CCl3−COOH

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11. The formation of cyanohydrin from an aldehyde is an example of:
(A) nucleophilic addition
(B) electrophilic addition
(C) nucleophilic substitution
(D) electrophilic substitution
Assertion−Reason questions:

1. Assertion (A): Acetic acid but not formic acid can be halogenated in presence of red P and
Cl2.
Reason (R): Acetic acid is a weaker acid than formic acid.
2. Assertion (A): Strong oxidising agents oxidise toluene and its derivatives to benzoic acids.
Reason (R): It is possible to stop the oxidation of toluene at the aldehyde stage with suitable
reagents.
3. Assertion (A): The pKa of ethanoic acid is lower than that of Cl−CH2−COOH.
Reason (R): Chlorine shows electron withdrawing (−I) effect which increases the acidic
character of Cl−CH2−COOH.
Very short answer type questions:
1. Do the following conversations in not more than 2 steps:
(a) CH3CN to CH3COCH3
(b) Benzoic acid to benzene

2. (a) Out of p-tolualdehyde and p-nitrobenzaldehyde, which one is more reactive towards
nucleophilic addition reactions, why?
(b) Write the structure of the product formed when acetone reacts with 2,4 DNP reagent.
3. Convert the following:
(a) Benzene to m-nitrobenzaldehyde
(b) Bromobenzene to benzoic acid

4. A and B are two functional isomers of compound C3H6O. On heating with NaOH and I2,
isomer B forms a precipitate of iodoform whereas isomer A does not form any precipitate.
Write the formulae of A and B.

5. Use Grignard reagent to prepare−

(a) Acetone to Tert−butyl alcohol
(b) Acetaldehyde to butan−2−ol

6. (a) Arrange the following compounds in the increasing order of their acidic strength:

(b) Write the IUPAC name of the given compound:

CH3COCH2COCH3

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Short answer type questions:
1. Compound (A) (C6H12O2) on reduction with LiAlH4 gives two compounds (B) and (C). The
compound (B) on oxidation with PCC gives compound (D) which upon treatment with dilute
NaOH and subsequent heating gives compound (E). Compound (E) on catalytic hydrogenation
gives compound (C). the compound (D) is oxidized further to give compound (F) which is found
to be a monobasic acid (Molecular weight = 60). Identify the compounds (A), (B), (C), (D), (E)
and (F).

2. How will you bring about the following conversions? (any three)
(a) Benzoic acid to benzaldehyde
(b) Ethanal to propanone
(c) Acetophenone to Benzoic acid
(d) Bromoebnzene to 1−phenylethanol

3. (a) Give chemical tests to distinguish between the following pairs of compounds:
(i) Phenol and benzoic acid
(ii) Propanal and Propanone
(b) Which one of the given compounds is a stronger acid and why?
CH2FCH2CH2COOH or CH3CHFCH2COOH

4. Give the structure of the major product expected from the following reactions:
(a) Reaction of ethanal with methyl magnesium bromide followed by hydrolysis.
(b) Hydration of But−1−ene in presence of dilute sulphuric acid.
(c) Reaction of phenol with bromine water.

5. Draw the structures major product(s) in each of the following reactions:

6. (a) Explain why?

(i) Carboxyl group in benzoic acid is meta directing.
(ii) Sodium bisulphite is used for the purification of aldehydes and ketones.
(iii) Carboxylic acids do not give characteristic reactions of carbonyl group.
OR
(b) An organic compound ‘A’, having the molecular formula C3H8O on treatment with Cu
at 573 K gives ‘B’. ‘B’ does not reduce Fehling’s solution but gives a yellow precipitate of
compound ‘C’ with I2/NaOH. Deduce the structures of A, B and C.

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7. An organic compound ‘X’ with molecular formula C5H10O forms 2,4−DNP derivative,
does not reduce Tollen’s reagent but keeps positive iodoform test on heating with I2 in
presence of NaOH. Compound ‘X’ gives ethanoic acid and propanoic acid on vigorous
oxidation. Write the –
(a) Structure of the compound ‘X’.
(b) Structure of the product obtained when compound ‘X’ reacts with 2,4−DNP reagent.
(c) Structures of the products obtained when compound ‘X’ is heated with I2 in presence
of NaOH.

8.

OR

(a) (i) Oxidation of propanal is easier than propanone. Why?

(ii) How can you distinguish between Acetophenone and Benzophenone?
(iii) Draw the structure of the following derivative:
2,4-Dinitrophenylhydrazone of propanone.
9. (a) Write the equations involved in the following reactions:
(i) Rosenmund reduction
(ii) Etard reaction
(iii) Stephen reaction
OR
(b) (i) Which acid of each pair would you expect to be stronger? Give reason.

10. (a) What happens when

(i) Propanone is treated with CH3Mg Br and then hydrolysed?
(ii) Ethanal is treated with excess ethanol and acid?
(iii) Methanal undergoes Cannizzaro reaction?
OR

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 (b) Write the main product in the following reactions:

11. (a) Which acid of the following pair would you expect to be stronger?
(i) F−CH2−COOH or CH3−COOH
(ii) Arrange the following compounds in the increasing order of the boiling points:
CH3CH2OH, CH3−CHO, CH3−COOH
(iii) Give simple chemical test to distinguish between Benzaldehyde and
Acetophenone.
OR
(b) (i) Which will undergo faster nucleophilic addition reaction?
Acetophenone or Propanone
(ii) What is the composition of Fehling’s solution?
(iii) Draw structure of the semicarbazone of Ethanal.

12. You are given four organic compounds “A, “B”, “C” and “D”. The compounds “A”, “B”
and “C” form an orange- red precipitate with 2,4 DNP reagent. Compounds “A” and “B”
reduce Tollen’s reagent while compounds “C” and “D” do not. Both “B” and “C” give a
yellow precipitate when heated with iodine in the presence of NaOH. Compound “D” gives
brisk effervescence with sodium bicarbonate solution. Identify “A”, “B”, “C” and “D”
given the number of carbon atoms in three of these carbon compounds is three while one
has two carbon atoms. Give an explanation for your answer.

Case based questions:

Read the passage properly and answer the following questions:

1. Aldol addition takes place whenever an aldehyde or ketone having atleast one  -H atom
is treated with dil NaOH or acid. The product is  hydroxyl aldehyde or ketone. On heating
loses a water molecule and give ,  unsaturated aldehyde or ketone. It is aldol
condensation. Aldehydes having no  -H also involve in the reaction in combination with
another aldehyde or ketone with  -H atom.

(a) PhCHO does not give aldol condensation product. Why?

(b) Write the product formed when 1 mole of HCHO is treated with 1 mole of
CH3CHO in presence of dilute NaOH.

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 (c) Identify A and B −

OR
(c) Identify P and Q −

2. Aldehydes, ketones and carboxylic acids are some of the important classes of organic
compounds containing carbonyl group. These are highly polar molecules due to higher
electronegativity of oxygen relative to carbon in the carbonyl group. Aldehydes are
prepared by dehydrohalogenation or controlled oxidation of primary alcohols and
controlled reduction of acyl halides. Ketones are prepared by oxidation of secondary
alcohols and hydration of alkynes.
Aldehydes and ketones undergo nucleophilic addition reactions onto the carbonyl group
but carboxylic acid does not undergo nucleophilic addition reaction. The alpha- hydrogens
of aldehydes and ketones are acidic. Therefore, aldehydes and ketones having at least one
alpha-hydrogen undergo aldol condensation.
Aldehydes are easily oxidised by mild oxidising agents such as Tollen’s reagent and
Fehling’s reagent. Carboxylic acids are prepared by the oxidation of primary alcohols,
aldehydes and by hydrolysis of nitriles. Aromatic carboxylic acids are prepared by side
chain oxidation of alkyls benzenes. Carboxylic acids are considerably more acidic than
alcohols and most of simple phenols.

(a) Arrange the following in the increasing order of their reactivity towards nucleophilic
addition reaction: CH3COCH3, CH3CHO, HCHO, C6H5COCH3
(b) Give a simple chemical test to distinguish between ethanal and propanone.
(c) Why carboxylic acid does not give nucleophilic addition reactions like aldehyde and
ketones?
(d) (i) Why α-hydrogen of aldehydes and ketones are acidic in nature?
(ii) Write the products in the following:

OR
Write the major products of the following reactions:

i.

ii.

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Long Answer Type Questions:
1. (a) Arrange the following compounds according to their increasing order of reactivity
towards nucleophilic addition reaction

(b) Write the IUPAC name of the product formed when butanone is reduced by LiAlH4.
(c)

Identify ‘B’ and ’C’

(d)

Identify ‘P’ and ‘Q’

2. An organic compound with molecular formula C7H7NO2 exists in three isomeric forms, the
isomer ‘A’ has the highest melting point of the three. ‘A’ on reduction gives compound ‘B’
with molecular formula C7H9N. ‘B’ on treatment with NaNO2/HCl at 0-5 0C to form
compound ‘C’. On treating C with H3PO2,it gets converted to D with formula C7H8, which
on further reaction with CrO2Cl2 followed by hydrolysis forms ‘E’ C7H6O. Write the
structure of compounds A to E. Write the chemical equations involved.

3. A hydrocarbon (A) with molecular formula C5H10 on ozonolysis gives two products (B)
and (C). Both (B) and (C) give a yellow precipitate when heated with iodine in presence of
NaOH while only (B) give a silver mirror on reaction with Tollen’s reagent.
(a) Identify (A), (B) and (C).
(b) Write the reaction of B with Tollen’s reagent
(c) Write the equation for iodoform test for C
(d) Write down the equation for aldol condensation reaction of B and C.
OR

An organic compound (A) with molecular formula C2Cl3O2H is obtained when (B) reacts
with Red P and Cl2. The organic compound (B) can be obtained on the reaction of methyl
magnesium chloride with dry ice followed by acid hydrolysis.
(a) Identify A and B
(b) Write down the reaction for the formation of A from B. What is this reaction called?
(c) Give any one method by which organic compound B can be prepared from its
corresponding acid chloride.
(d) Which will be the more acidic compound (A) or (B)? Why?
(e) Write down the reaction to prepare methane from the compound (B).

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4. Account for the following:
(a) Oxidation of aldehydes is easier as compared to ketones.
(b) The alfa hydrogen of aldehydes is acidic in nature.
(c) Write the products of the following reactions:

(i)

(ii)

(iii) Give a simple test to distinguish between ethanoic acid and ethanal.

5. (a) Write the major product(s) in the following reactions :

(i)

(ii)

(iii)
(b) Give simple chemical tests to distinguish between the following pairs of compounds:

(i)
(ii) Pentanal and Pentan-3-one.

OR
(a) Give reasons for the following:
(i) In semicarbazide, only one −NH2 group is involved in the formation of
semicarbazone.
(ii) Acetaldehyde is more reactive than acetone towards addition of HCN.
(b) Arrange the following in decreasing order of their acidic strength :
CH3COOH, O2N−CH2−COOH, HCOOH
(c) Name the reagent in the following reaction:

(d) Write the reaction involved in Hell-Volhard-Zelinsky reaction.

6. (a) An organic compound (X) having molecular formula C5H10O can show various
properties depending on its structures. Draw each of the structures if it

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 (i) gives positive iodoform test.
(ii) Shows Cannizzaro’s reaction.
(iii) Reduces Tollens’ reagent and has a chiral carbon.
(b) Write the reaction involved in the following:
(i) Wolff-Kishner reduction
(ii) Hell-Volhard-Zelinsky reaction.

OR
(a) How can you convert each of the following compounds to Benzoic acid ?
(i) Acetophenone
(ii) Ethylbenzene
(iii) Bromobenzene
(b) Arrange the following compounds in increasing order of their property as
indicated :
(i) O2N−CH2−COOH, F−CH2−COOH, CN−CH2−COOH (Acidic character)
(ii) Ethanal, Propanal, Butanone, Propanone (Reactivity in nucleophilic addition
reactions)

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