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All questions of Aldehydes, Ketones and Carboxylic Acids for JEE Exam

When CH2 = CH — COOH is reduced with LiAlH4, the compound obtained will be
  • a)
    CH2 = CH — CH2OH
  • b)
    CH3 — CH2 — CH2OH
  • c)
    CH3 — CH2 — CHO
  • d)
    CH3 — CH2 — COOH
Correct answer is option 'A'. Can you explain this answer?

Prasad Mehra answered
Explanation:

Reduction of CH2 = CH — COOH with LiAlH4:
- When CH2 = CH — COOH is reduced with LiAlH4, the carbonyl group (COOH) is reduced to an alcohol group (CH2OH).
- LiAlH4 is a strong reducing agent that can reduce carbonyl groups to alcohols.

Obtained Compound:
- The compound obtained after reduction will be CH2 = CH — CH2OH.
- The double bond remains intact while the carbonyl group is reduced to an alcohol group.
Therefore, the correct answer is option 'A' - CH2 = CH — CH2OH.

Which of the following compounds will react with ethanolic KCN?
  • a)
    ethyl chloride
  • b)
    acetyl chloride
  • c)
    chlorobenzene
  • d)
    benzaldehyde
Correct answer is option 'A,B,D'. Can you explain this answer?

Poulomi Datta answered
The given reaction is a nucleophilic substitution reaction. 
With ethanolic KCN, allyl bromide and ethyl bromide reacts to form nitrile compound. Chlorobenzene and vinyl bromide does not react as they have = bond and the bond is shorter and stronger cann't be replaced by CN group.

The enolic form of acetone contains
  • a)
    9 sigma bonds, 1 pi-bond and 2 lone pairs
  • b)
    8 sigma bonds, 2 pi-bonds and 2 lone pairs
  • c)
    10 sigma bonds, 1 pi-bond and 1 lone pair
  • d)
    9 sigma bonds, 2 pi-bonds and 1 lone pair
Correct answer is option 'A'. Can you explain this answer?

Ameya Mishra answered
The enolic form of acetone refers to the structure of acetone when it exists in its enol tautomeric form. In this form, one of the carbonyl oxygen atoms in acetone is protonated, resulting in the formation of an enol group (-C=C-OH). Let's break down the structure and analyze the number of sigma bonds, pi-bonds, and lone pairs in the enolic form of acetone.

Structure of the enolic form of acetone:
CH3-C(=C(OH))-CH3

The structure can be divided into three parts: the methyl group (-CH3), the double bond (C=C), and the hydroxyl group (-OH).

Counting sigma bonds:
- The methyl group has three sigma bonds: one C-C bond and two C-H bonds.
- The double bond has one sigma bond between the carbon atoms (C=C).
- The hydroxyl group has three sigma bonds: one C-O bond and two O-H bonds.

Therefore, the total number of sigma bonds in the enolic form of acetone is 3 + 1 + 3 = 7.

Counting pi-bonds:
- The double bond (C=C) consists of one pi bond.

Therefore, the enolic form of acetone has 1 pi-bond.

Counting lone pairs:
- The oxygen atom in the hydroxyl group has two lone pairs.

Therefore, the enolic form of acetone has 2 lone pairs.

Summarizing the results:
- The enolic form of acetone has a total of 7 sigma bonds (3 from the methyl group, 1 from the double bond, and 3 from the hydroxyl group).
- It also has 1 pi-bond (from the double bond) and 2 lone pairs (from the oxygen atom in the hydroxyl group).

Hence, option A is the correct answer, as it correctly states that the enolic form of acetone contains 9 sigma bonds (7 from the atoms and 2 from the methyl groups), 1 pi-bond (from the double bond), and 2 lone pairs (from the oxygen atom in the hydroxyl group).

Which one of the following is reduced with zinc and hydrochloric acid to give the corresponding hydrocarbon?
  • a)
    Acetamide
  • b)
    Acetic acid
  • c)
    Ethyl acetate
  • d)
    Butan-2-one
Correct answer is option 'D'. Can you explain this answer?

To determine which compound can be reduced with zinc and hydrochloric acid to give the corresponding hydrocarbon, we need to understand the process of reduction and the properties of the given compounds.

Reduction with Zinc and Hydrochloric Acid:
The reduction of a compound with zinc and hydrochloric acid involves the transfer of hydrogen atoms from the reducing agents (zinc and hydrochloric acid) to the compound, resulting in the formation of a hydrocarbon.

Given Compounds:
a) Acetamide
b) Acetic acid
c) Ethyl acetate
d) Butan-2-one

To identify the compound that can be reduced, we need to consider the presence of functional groups and the reactivity of these functional groups towards reduction.

Acetamide:
Acetamide contains an amide functional group (RCONH2). Amides are not easily reduced by zinc and hydrochloric acid. They require stronger reducing agents or harsher conditions. Therefore, acetamide is not likely to be reduced to a hydrocarbon by zinc and hydrochloric acid.

Acetic Acid:
Acetic acid contains a carboxylic acid functional group (RCOOH). Carboxylic acids can be reduced to aldehydes or alcohols, but they are not directly converted to hydrocarbons by zinc and hydrochloric acid. Therefore, acetic acid is not likely to be reduced to a hydrocarbon in this reaction.

Ethyl Acetate:
Ethyl acetate contains an ester functional group (RCOOR'). Esters can be reduced to alcohols, but they are not directly converted to hydrocarbons by zinc and hydrochloric acid. Therefore, ethyl acetate is not likely to be reduced to a hydrocarbon in this reaction.

Butan-2-one:
Butan-2-one contains a ketone functional group (RCOCH3). Ketones can be reduced to secondary alcohols or further reduced to hydrocarbons by zinc and hydrochloric acid. Therefore, butan-2-one can be reduced with zinc and hydrochloric acid to give the corresponding hydrocarbon.

Therefore, the correct answer is option D) Butan-2-one.

The increasing order of the rate of HCN addition to compound A – D is
(A) HCHO
(B) CH3COCH3
(C) PhCOCH3
(D) PhCOPh
  • a)
    D < C < B < A
  • b)
    C < D < B < A
  • c)
    A < B < C < D
  • d)
    D < B < C < A
Correct answer is option 'A'. Can you explain this answer?

Sahana Ahuja answered
NOTE : Addition of HCN to carbonyl compounds is nucleophilic addition reaction. The order of reactivity of carbonyl compounds is Aldehydes (smaller to higher) Ketones (smaller to higher), Then                    
HCHO > CH3COCH3 > Ph.COCH3 > PhCOPh
NOTE : The lower reactivity of Ketones is due to presence of two alkyl group which shows +I effect.
The reactivity of Ketones decreases as the size of alkyl group increases.

Which one of the following will most readily be dehydrated in acidic condition ?
  • a)
  • b)
  • c)
  • d)
Correct answer is option 'A'. Can you explain this answer?

Baby Ghosh answered
Yeah..It will be option A...That compund will undergoes readily in acidic medium..because that compound is more stable than other compounds.

In the given transformation, which of the following is the most appropriate reagent ?
  • a)
  • b)
    Zn – Hg/ HCl
  • c)
    Na, Liq NH3
  • d)
    NaBH4
Correct answer is option 'A'. Can you explain this answer?

Ruchi Yadav answered
Aldehydes and ketones canbereduced to hydrocarbons by the action (i) of amalgamated zinc and concentrated hydrochloric acid (Clemmensen reduction), or (b) of hydrazine (NH2NH2) and a strong base like NaOH, KOH or potassium tert-butoxide in a high-boiling alcohol like ethylene glycol or triethylene glycol (Wolf-Kishner reduction)

A mixture of benzaldehyde and formaldehyde on heating with aqueous NaOH solution gives
  • a)
    benzyl alcohol and sodium formate
  • b)
    sodium benzoate and methyl alcohol
  • c)
    sodium benzoate and sodium formate
  • d)
    benzyl alcohol and methyl alcohol
Correct answer is option 'A'. Can you explain this answer?

Jatin Dasgupta answered
TIPS/Formulae : Both compounds do not contain a-hydrogen hence undergo Crossed Cannizzaro reaction.
Initially OH- attacks at the carbonyl carbon of HCHO than that of PhCHO because carbonyl carbon of HCHO is
(i) more el ectrophilic
(ii) less sterically hindered to give hydroxyalkoxide which acts as hydride donor in next step to give sodium formate.

Which of the following compounds will give a yellow precipitate with iodine and alkali?
  • a)
    2-Hydroxypropane
  • b)
    acetophenone
  • c)
    methyl acetate
  • d)
    acetamide
Correct answer is option 'A,B'. Can you explain this answer?

Kajal Iyer answered
Answer:

Introduction:
In this question, we are asked to determine which of the given compounds will give a yellow precipitate with iodine and alkali. The reaction of iodine with alkali forms a complex, which is typically yellow in color. Let's analyze each compound and determine if it will give a yellow precipitate.

Analysis:

a) 2-Hydroxypropane:
2-Hydroxypropane is an alcohol, which contains a hydroxyl group (-OH). When this compound reacts with iodine and alkali, the hydroxyl group can oxidize to form a carbonyl compound. The carbonyl compound can further react with iodine to form a yellow precipitate. Therefore, 2-Hydroxypropane is expected to give a yellow precipitate.

b) Acetophenone:
Acetophenone is a ketone, which contains a carbonyl group (>C=O). Ketones do not react with iodine and alkali to form a yellow precipitate. Therefore, Acetophenone is not expected to give a yellow precipitate.

c) Methyl acetate:
Methyl acetate is an ester, which contains an ester functional group (-COO-). Esters do not react with iodine and alkali to form a yellow precipitate. Therefore, Methyl acetate is not expected to give a yellow precipitate.

d) Acetamide:
Acetamide is an amide, which contains an amide functional group (-CONH2). Amides do not react with iodine and alkali to form a yellow precipitate. Therefore, Acetamide is not expected to give a yellow precipitate.

Conclusion:
Based on the analysis, the compounds that are expected to give a yellow precipitate with iodine and alkali are 2-Hydroxypropane and Acetophenone. Therefore, the correct answer is option A and B.

PASSAGE-4
In the following reaction sequence, the compound J is an intermediate.
J (C9H8O2) gives effervescence on treatment with NaHCO3 and a positive Baeyer’s test.
Q. The compound I is
  • a)
  • b)
  • c)
  • d)
Correct answer is option 'C'. Can you explain this answer?

Ishita Reddy answered
Reactions of compound J (C9H8O2) indicates that  it has C = C linkage and – COOH group. Thus, J can be written as C6H5CH = CH COOH. Since, J is unsaturated carboxylic acid and it is formed by the reactions of compound I with (CH3CO)2O and CH3COONa, compound I should be an aldehyde (recall Perkin reaction). Thus the whole series of reactions can be written as below.


In the following reaction sequence, product I, J and L are formed.
K represents a reagent.
Q. The structure of product L is
  • a)
  • b)
  • c)
  • d)
Correct answer is option 'C'. Can you explain this answer?

Sahana Joshi answered
It is Rosemmund reaction. Simultaneously the reagent H2-Pd also reduces carbon-carbon triple bond to double bond (syn -addition) giving cis product.

Ethyl ester  The product P will be
  • a)
  • b)
  • c)
  • d)
Correct answer is option 'A'. Can you explain this answer?

Pranav Pillai answered
Recall that, esters react with excess of Grignard reagents to form 3º alcohols having at least two identical alkyl groups corresponding to Grignard reagent.

An enantiomerically pure acid is treated with a racemic mixture of an alcohol having one chiral carbon. The ester formed will be
  • a)
    Optically active mixture
  • b)
    Pure enantiomer
  • c)
    Meso compound
  • d)
    Racemic mixture
Correct answer is option 'A'. Can you explain this answer?

Atharva Pillai answered
The optically active acid will react with d and l forms of alcohol present in the racemic mixture at different rates to form two diastereomers in unequal amounts leading to optical activity of the product.

Polarisation of electrons in acrolein may be written as
  • a)
  • b)
  • c)
  • d)
Correct answer is option 'D'. Can you explain this answer?

Krish Ghoshal answered
NOTE : –CHO produces –R effect i.e. it withdraws electrons from the double bond or from a conjugated system towards itself.

The compound (X) is
  • a)
    CH3COOH
  • b)
    BrCH2 - COOH
  • c)
    (CH3CO)2O
  • d)
    CHO - COOH
Correct answer is option 'C'. Can you explain this answer?

TIPS/Formulae : This reaction is an example of “Perkin reaction”.
The compound X should be (CH3CO)2O.
In this step the carbanion is obtained by removal of an α–H atom from a molecule of an acid anhydride, the anion of the corresponding acid acting as a necessary base.

PASSAGE-2
A carbonyl compound P,  which gives positive iodoform test, undergoes reaction with MeMgBr followed by dehydration to give an olefin Q. Ozonolysis of Q leads to a dicarbonyl compound R, which undergoes intramolecular aldol reaction to give predominantly S.
Q. The structures of the products Q and R, respectively, are
  • a)
  • b)
  • c)
  • d)
Correct answer is option 'A'. Can you explain this answer?

Aryan Sen answered
Iodoform test of compound P points out that P has – COCH3 group which shows that it may be either option (a) or (b) of Q. 16. Further since the dicarbonyl compound R has at least one a-H atom w.r.t to one of the carbonyl groups which is possible when R is produced from (b) of Q. 18; (a) option of Q. 16 will give dicarbonyl compound having two –CHO, none of which has a-H atom.



* Structure of R would be R' when P is (A)

Th e correct order of increasing acid stren ght of the compounds
(A) CH3CO2H
(B) MeOCH2CO2H
(C) CF3CO2H
is
  • a)
    D < A < B < C
  • b)
    A < D < B < C
  • c)
    B < D < A < C
  • d)
    D < A < C < B
Correct answer is option 'A'. Can you explain this answer?

Gauri Chauhan answered
The correct order of increasing acid strength
CF3 . COOH > MeOCH2COOH > CH3COOH > (Me)2CH.COOH
[NOTE : Electron withdrawing groups increase the acid strength and electron donating groups decrease the acid strength.]

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