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

The IUPAC name of CH3CHO is:
  • a)
    Acetaldehyde
  • b)
    Ethanal
  • c)
    Formaldehyde
  • d)
    Methanal
Correct answer is option 'A'. Can you explain this answer?

  • The functional group is an aldehyde; −CHO and the given compound has two carbon atoms.
  • Thus, the IUPAC name of the compound is ethanal.

 Which of the following statements are correct in case of the carbonyl bond between carbon and oxygen?
  • a)
    Carbon is the nucleophilic centre and Oxygen is the electrophilic centre.
  • b)
    Oxygen is the nucleophilic centre and Carbon is the electrophilic centre.
  • c)
    Carbon and Oxygen double bond is polarised.
  • d)
    Both ‘b’ and ‘c’ are correct
Correct answer is option 'C'. Can you explain this answer?

Nandini Patel answered
The double bonds in alkenes and double bonds in carbonyl groups are VERY different in terms of reactivity. The C=C is less reactive due to C=O electronegativity attributed to the oxygen and its two lone pairs of electrons.  One pair of the oxygen lone pairs are located in 2s while the other pair are in 2p orbital where its axis is directed perpendicular to the direction of the pi orbitals.  The Carbonyl groups properties are directly tied to its electronic structure as well as geometric positioning.  For example, the electronegativity of oxygen also polarizes the pi bond allowing the single bonded substituent connected to become electron withdrawing.

 Which of the following statement about C=O and C=C is correct?
  • a)
    Both consist of a sigma and pi bond
  • b)
    C=O is polar but C=C is non-polar
  • c)
    Both a and b are correct
  • d)
    Both C=O and C=C undergo nucleophilic addition reactions
Correct answer is option 'C'. Can you explain this answer?

Knowledge Hub answered
  • The first bond formed is a sigma bind and the second one is a pi bond.
  • O has a higher electronegativity than C and hence the electron cloud will be shifted towards the O atom, making the compound polar.
  • This is not possible in C=C.

What is the IUPAC name of Acrolein?
  • a)
    pent-2-enal
  • b)
    but-1-enal
  • c)
    prop-2-enal
  • d)
    but-2-enal
Correct answer is option 'C'. Can you explain this answer?

Nandini Iyer answered
IUPAC name of acrolein is prop-2-enal, a name derived from that of acrylic acid, the parent carboxylic acid.

Propanone and prop-2-en-1-ol are examples of which type of isomerism?
  • a)
    Functional isomers
  • b)
    Chain isomers
  • c)
    Tautomers
  • d)
    Position isomers
Correct answer is option 'A'. Can you explain this answer?

Functional isomers

Explanation: Propanone (CH3COCH3) and prop-2-en-1-ol (CH2=CHCH2OH) are examples of functional isomers because they have the same molecular formula (C3H6O) but different functional groups. Propanone has a carbonyl group (C=O) while prop-2-en-1-ol has an alcohol group (OH) and a carbon-carbon double bond (C=C).

What is the common name of 2-methyl-propanal?
  • a)
    formaldehyde
  • b)
    Isobutyraldehyde
  • c)
    carbaldehyde
  • d)
    acetaldehyde
Correct answer is 'B'. Can you explain this answer?

Nikita Singh answered
  • Isobutyraldehyde is the chemical compound with the formula (CH₃)₂CHCHO.
  • It is an aldehyde, isomeric with n-butyraldehyde.
  • Isobutyraldehyde is manufactured, often as a side-product, by the hydroformylation of propene. Its odour is described as that of wet cereal or straw.

An organic compound A (C7H16O) shows both enantiomerism and diastereomerism. Treatment of a pure enantiomer of A with Na2CrO4 /Dil. H2SO4 gives B (C7H14O) - Also A on dehydration with concentrated H2SO4 gives a single alkene C (C7H14). Ozonolysis of C followed by work-up with Zn-H2O gives D (C5H10O) as one of the product which gives racemic mixture on reduction with NaBH4.
Q. 
If B is reduced with LiAIH4 followed by acid hydrolysis will give
  • a)
    a pure enantiomer
  • b)
    a racemic mixture
  • c)
    a pair of diastereomers
  • d)
    an achiral alcohol
Correct answer is option 'C'. Can you explain this answer?

Preethi Kaur answered
Explanation:

Enantiomerism:
Enantiomerism refers to the phenomenon where two molecules are mirror images of each other and are non-superimposable. In this case, compound A shows enantiomerism, which means it exists in two different mirror-image forms.

Diastereomerism:
Diastereomerism refers to the phenomenon where two molecules have the same connectivity but are not mirror images of each other and are non-superimposable. In this case, compound A shows diastereomerism, which means it exists in multiple forms that are not mirror images of each other.

Reaction 1: Treatment of A with Na2CrO4/Dil. H2SO4:
When compound A is treated with Na2CrO4 and dilute H2SO4, it undergoes oxidation reaction and gives compound B. The reaction is as follows:

C7H16O (A) + Na2CrO4 / Dil. H2SO4 → C7H14O (B)

Reaction 2: Dehydration of A with concentrated H2SO4:
When compound A is dehydrated with concentrated H2SO4, it undergoes elimination reaction and gives a single alkene C. The reaction is as follows:

C7H16O (A) + H2SO4 (conc.) → C7H14 (C)

Reaction 3: Ozonolysis of C followed by work-up with Zn-H2O:
When alkene C is subjected to ozonolysis followed by treatment with Zn-H2O, it undergoes oxidative cleavage and gives compound D as one of the products. The reaction is as follows:

C7H14 (C) + O3 → C5H10O (D)

Reaction 4: Reduction of D with NaBH4:
When compound D is reduced with NaBH4, it undergoes reduction reaction and gives a racemic mixture. This means that both enantiomers of D are formed in equal amounts. The reaction is as follows:

C5H10O (D) + NaBH4 → Racemic mixture of D

Reaction 5: Reduction of B with LiAlH4 followed by acid hydrolysis:
When compound B is reduced with LiAlH4 followed by acid hydrolysis, it undergoes reduction reaction and gives a pair of diastereomers. This means that two different diastereomers of B are formed. The reaction is as follows:

C7H14O (B) + LiAlH4 → Diastereomers of B

Therefore, the correct answer is option c) a pair of diastereomers.

Comprehension Type
Direction (Q. Nos. 20-22) This section contains a paragraph, describing theory, experiments, data, etc.
Three questions related to the paragraph have been given. Each question has only one correct answer among the four given options (a), (b), (c) and (d).
Passage
Aldol condensation is an important reaction in organic chemistry, particularly for the formation of carbon-carbon bonds. This reaction typically involves the enolate ion derived from an aldehyde or ketone reacting with another carbonyl compound to form a β-hydroxy aldehyde or β-hydroxy ketone. This product can undergo dehydration to form an α,β-unsaturated carbonyl compound. The reaction is usually catalyzed by a base, although acid-catalyzed versions are also known. The presence of at least one α-hydrogen in the reactant is crucial for the aldol condensation to occur. Acetaldehyde, for example, can undergo aldol condensation to yield 3-hydroxybutanal, which can then dehydrate to form crotonaldehyde.
Ques: In the aldol condensation reaction of acetaldehyde (CH₃CHO), the initial product formed before dehydration is:
  • a)
    2-Hydroxybutanal
  • b)
    Crotonaldehyde
  • c)
    3-Hydroxybutanal
  • d)
    Acetone
Correct answer is option 'C'. Can you explain this answer?

Om Kumar answered
The initial product formed in the aldol condensation reaction of acetaldehyde (CH₃CHO) is 3-hydroxybutanal. Here’s how:
  • Acetaldehyde (CH₃CHO) has an α-hydrogen, which is necessary for forming the enolate ion.
  • The enolate ion then reacts with another acetaldehyde molecule.
  • This reaction forms 3-hydroxybutanal as the initial product
  • Crotonaldehyde is formed after the dehydration of 3-hydroxybutanal.
Correct Answer: c

Consider the isomeric aldehydes with molar mass 100, if all the isomers (only structural) are treated independently with NH2OH, how many of them would give more than two stereomeric oximes?
    Correct answer is '3'. Can you explain this answer?

    Janhavi Kaur answered
    MW = 100 indicates that molecular formula of aldehyde is C6H12O . For obtain ing more than two oximes, aldehyde must exist stereomeric.

    All the above has one chiral carbon each. Hence, when reacted with H2NOH, forms more than two oximes.

    Which can be deduced correctly regarding keto-enol tautomerism in general?
    • a)
      Increasing temperature increases the enol content at equilibrium
    • b)
      Mono-enols are usually more stable than dienols
    • c)
      Enols of ketones are generally more stable than enols of aliphatic aldehydes
    • d)
      Keto-enol taytomerism is catalysed by both acidic and basic catalys
    Correct answer is option 'A,B,C,D'. Can you explain this answer?

    Increasing temperature increases equilibrium content of less stable enol tautomers.
    Enolisation decreases stability, hence introducing two or more enol groups are further more difficult.
    Enols of ketones are more substituted at double bond, hence more stable.
    Both acid and base catalyses keto-enol tautomerism.

    The compound(s) below that gives yellow precipitate with KOH/I2 is/are
    • a)
      CH3CH2OH
    • b)
    • c)
    • d)
      Cl—CH2—CHO
    Correct answer is option 'A,C'. Can you explain this answer?

    Shraddha Gupta answered
    Aldehydes and ketones with  groups form iodoform with NaOH/I2. Besides, aldehydes and ketones, alcohols with group also form iodofom in the same reaction.

    What is the correct order of equilibrium enol content of the following compounds?
    I. CH3COCH3
    II. CH3COCH2COOC2H5
    III. CH3COCH2COCH3
    IV. CH3COCH2COH
    • a)
      I > II > III > IV
    • b)
      I > IV > III > II
    • c)
      IV > II > III > I
    • d)
      III > IV > II > I
    Correct answer is option 'D'. Can you explain this answer?

    Asha Nair answered
    A 1,3-diketo compound forms more stable enol than a monocarbonyls. Also ester group forms less stable enol than carbonyls. Hence, III, a 1 , 3-diketo ne form s highest enol content while I (monocarbonyl) forms least enol content at equilibrium.

    Only One Option Correct Type
    Direction (Q. Nos. 1-14) This section contains 14 multiple choice questions. Each question has four choices (a), (b), (c) and (d), out of which ONLY ONE is correct.
    Q. 
    In hexane-2,4-dione, how many different mono-enols are possible?
    • a)
      2
    • b)
      3
    • c)
      4
    • d)
      7
    Correct answer is option 'D'. Can you explain this answer?

    Devanshi Mehta answered
    Possible Mono-enols in Hexane-2,4-dione

    Hexane-2,4-dione, also known as Acetylacetone, has the following structure:

    CH3COCH2COCH3

    Mono-enol is the product obtained when one enolizable hydrogen atom of a compound is replaced by a hydroxyl group (-OH).

    To determine the number of different mono-enols possible in hexane-2,4-dione, we need to identify the enolizable hydrogen atoms. These are the hydrogen atoms attached to the carbon atoms that are adjacent to the carbonyl groups (-CO-).

    In hexane-2,4-dione, there are two such hydrogen atoms, one on each side of the molecule. Therefore, there are two possible enols that can be formed:

    - The first enol is formed by replacing the hydrogen atom attached to the carbon atom adjacent to the ketone (-CO-) group on the left side of the molecule. This enol is called the alpha-enol or 1-enol.

    CH3COCH=C(OH)CH3

    - The second enol is formed by replacing the hydrogen atom attached to the carbon atom adjacent to the ester (-COO-) group on the right side of the molecule. This enol is called the beta-enol or 3-enol.

    CH3C(OH)=CHCOCH3

    However, each of these enols can exist in two different tautomeric forms: keto and enol. Tautomerism is the phenomenon where a compound exists in two or more isomeric forms that differ only in the position of a hydrogen atom and a double bond.

    - The keto form is the one in which the compound has a carbonyl group (-CO-) and no hydroxyl (-OH) group.
    - The enol form is the one in which the compound has a double bond (-C=C-) and a hydroxyl (-OH) group.

    Therefore, there are four possible mono-enols in hexane-2,4-dione:

    - The alpha-keto-enol form, also known as 1,3-diketone form.
    - The alpha-hydroxy-ketone form or 1-enol form.
    - The beta-keto-enol form, also known as the 3,5-diketone form.
    - The beta-hydroxy-ketone form or 3-enol form.

    However, each of these forms can also exist as a mixture of both tautomeric forms, keto and enol. Therefore, a total of seven different mono-enols are possible in hexane-2,4-dione:

    - Alpha-keto-enol form (1,3-diketone)
    - Alpha-enol-keto form (1-enol)
    - Alpha-enol-enol form (1-enol)
    - Beta-keto-enol form (3,5-diketone)
    - Beta-enol-keto form (3-enol)
    - Beta-enol-enol form (3-enol)
    - Beta-enol-enol-keto form (3-enol)

    Therefore, the correct answer is option D, seven.

    One or More than One Options Correct Type
    Direction (Q. Nos. 11-15) This section contains 5 multiple choice questions. Each question has four choices (a), (b), (c) and (d), out of which ONE or MORE THAN ONE are correct.
    Q. 
    Successful mixed aldol condensation will be favoured 
    • a)
      treatment of electrophilic carbonyl component with stoichiometric strong base prior to the addition of the pre-nucleophilic carbonyl component
    • b)
      treatment of mixture of electrophilic carbonyl component and pre-nucleophilic component with stoichiometric strong base
    • c)
      continuous removal of aldol product from reaction mixture
    • d)
      treatment of pre-nucleophilic carbonyl component with stoichiometric strong base prior to the addition of electrophilic carbonyl component.
    Correct answer is option 'C,D'. Can you explain this answer?

    For successful mixed aldol condensation to be favored, the correct conditions should ensure that one carbonyl component acts as a nucleophile while the other acts as an electrophile. Here's the analysis of each option:
    (a) Treatment of electrophilic carbonyl component with a stoichiometric strong base before the addition of the pre-nucleophilic carbonyl component
    • This would likely deprotonate the electrophilic carbonyl component, making it a poor electrophile and favoring side reactions. This is not favorable for a successful mixed aldol reaction.
      (Incorrect)
    (b) Treatment of mixture of electrophilic carbonyl component and pre-nucleophilic component with stoichiometric strong base
    • This could result in deprotonation on both components, leading to a mixture of products and possibly side reactions.
      (Incorrect)
    (c) Continuous removal of aldol product from the reaction mixture
    • Removing the aldol product shifts the equilibrium towards product formation, which is a beneficial condition for successful mixed aldol condensation.
      (Correct)
    (d) Treatment of pre-nucleophilic carbonyl component with stoichiometric strong base prior to the addition of electrophilic carbonyl component
    • This ensures that the pre-nucleophilic component forms an enolate, which can then attack the electrophilic carbonyl component without side reactions, favoring a successful aldol condensation.
      (Correct)
    Final Answer:
    (c) and (d) are correct choices.

    Which compound (s) below can react via an intramolecular aldol condensation to give a six membered ring?
    • a)
    • b)
    • c)
    • d)
    Correct answer is option 'A,C,D'. Can you explain this answer?

    Sinjini Tiwari answered
    All of these react in aldol reaction giving six-membered ring via intramolecular reaction.
    Option (b) gives five and seven membered ring intramolecular aldol condensation.

    A colourless liquid, at room temperature, reacts with soda-lime to form sodium salt of a carboxylic acid and ammonia gas. The liquid is
    • a)
      propanoic acid
    • b)
      formamide
    • c)
      propanamide
    • d)
      methyl enthanoate
    Correct answer is option 'B'. Can you explain this answer?

    Only amides (but not acids and esters) undergo hydrolysis in presence of soda-lime to form sodium salt of a carboxylic acid and ammonia gas. Further, since the given compound is a liquid, it must be formamide, because propanamide is a solid.

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