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All questions of Aldehydes, Ketones and Carboxylic Acids for NEET 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.

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.

CH3CHO and C6H5CH2CHO can be distinguished chemically by: [2012]
  • a)
    Benedict test
  • b)
    Iodoform test
  • c)
    Tollen’s reagent test
  • d)
    Fehling solution test
Correct answer is option 'B'. Can you explain this answer?

CH3CHO and C6H5CH2CHO both are aldehydes so they can give the test of Tollen’s reagent, Fehling's solution and Benedict’s solution.
The carbonyl compounds with the structure R-CO-CH3 can only give the Iodoform test.
CH3CHO is the only aldehyde which reacts with NaOH and I2 to give yellow crystals of Iodoform while C6H5CH2CHO doesn’t react with it. 
So, the iodoform test is used to distinguish between CH3CHO and C6H5CH2CHO compounds. 
CH3CHO + 3I+ 4NaOH ⟶ CHI+ HCOONa + 3NaI +3H2O
C6H5CH2CHO + I+ 4NaOH⟶ No reaction.

Propionic acid with Br2|P yields a dibromo product. Its structure would be: [2009]
  • a)
  • b)
    CH2Br – CH2 – COBr
  • c)
  • d)
    CH2 Br – CHBr – COOH
Correct answer is option 'C'. Can you explain this answer?

Anand Jain answered
This reaction is an example of Hell - Volhard
Zelinsky reaction. In this reaction acids
containing α– H on treatment with X2 /P
give di-halo substituted acid.

The oxidation of toluene to benzoic acid can be stopped at the aldehyde stage. The reaction is called?
  • a)
    Etard reaction
  • b)
    Stephen reaction
  • c)
    Friedel – crafts reaction
  • d)
    Gatterman – Koch reaction
Correct answer is option 'A'. Can you explain this answer?

Aryan Sen answered
Etard reaction

The oxidation of toluene to benzoic acid can be stopped at the aldehyde stage by using the Etard reaction. The Etard reaction is a chemical reaction that involves the oxidation of aromatic hydrocarbons using chromyl chloride (CrO2Cl2) as the oxidizing agent. This reaction is commonly used to convert alkylbenzenes, such as toluene, into their corresponding aldehydes.

Reaction Mechanism
The reaction proceeds through several steps:

1. Formation of the chromyl chloride complex: Chromyl chloride is formed by the reaction of chromic acid (H2CrO4) with sodium chloride (NaCl). The chromyl chloride complex acts as the oxidizing agent in the Etard reaction.

2. Activation of the aromatic ring: The aromatic ring of toluene is activated through the coordination of the chromyl chloride complex with the electron-rich aromatic system. This coordination weakens the carbon-hydrogen bonds adjacent to the aromatic ring, making them more susceptible to oxidation.

3. Oxidation of toluene to benzaldehyde: The activated toluene undergoes oxidation by the chromyl chloride complex, resulting in the formation of benzaldehyde. The chromyl chloride complex acts as a strong electrophile, attacking the activated carbon-hydrogen bond and forming a carbocation intermediate. This intermediate is then hydrolyzed to yield benzaldehyde.

4. Further oxidation to benzoic acid: If the reaction is allowed to continue, benzaldehyde can undergo further oxidation to form benzoic acid. However, to stop the reaction at the aldehyde stage, the reaction conditions can be carefully controlled, such as by adjusting the reaction temperature or using a milder oxidizing agent.

Applications
The Etard reaction has several applications in organic synthesis. It is commonly used for the selective oxidation of alkylbenzenes to their corresponding aldehydes, as demonstrated in the oxidation of toluene to benzaldehyde. This reaction is useful for the synthesis of various aromatic aldehydes, which are important intermediates in the preparation of pharmaceuticals, fragrances, and other organic compounds.

Conclusion
The oxidation of toluene to benzoic acid can be stopped at the aldehyde stage by using the Etard reaction. This reaction involves the oxidation of toluene to benzaldehyde using chromyl chloride as the oxidizing agent. By carefully controlling the reaction conditions, it is possible to halt the reaction at the aldehyde stage and prevent further oxidation to benzoic acid. The Etard reaction has important applications in organic synthesis, particularly in the preparation of aromatic aldehydes.

Arrange the following compounds in decreasing order of their acid strength: i) trichloroacetic acid ii) trifluoroacetic acid iii) acetic acid and iv) formic acid
  • a)
    trifluoroacetic acid, trichloroacetic acid, formic acid and acetic acid
  • b)
    formic acid., trifluoroacetic acid, trichloroacetic acid, and acetic acid
  • c)
    trichloroacetic acid, trifluoroacetic acid, acetic acid and formic acid.
  • d)
    trifluoroacetic acid, formic acid acetic acid and Propan – 1 – ol, 4 – methylphenol
Correct answer is option 'A'. Can you explain this answer?

Tanuja Kapoor answered
Acidic strength of carboxylic acid -
–  More acidic than phenols or alcohols.
–  Acidity increase with the presence of a group with  -I effect in the alkyl group.Whereas it decreases with the presence of  +I group.
–  Acidity increases with increase in the number of halogen atoms on  - position.
–  It decreases with increasing distance of halogen from   
–  It increases with increase in the electronegativity of halogen.
- CF3COOH > CCl3COOH > HCOOH > CH3 COOH

Iodoform test is not given by [1999]
  • a)
    2-Pentanone
  • b)
    Ethanol
  • c)
    Ethanal
  • d)
    3-Pentanone
Correct answer is option 'D'. Can you explain this answer?

Priyanka Iyer answered
Iodoform test is exhibited by ethyl alcohol acetaldehyde, acetone methyl ketones and those alcohols which possess CH3CH(OH)- group. As 3-pentanone does not contain
CH3CO-group as therefore it does not give iodoform test.

Which of the following is incorrect? [2001]
  • a)
    NaHSO3 is used in detection of carbonylcompound
  • b)
    FeCl3 is used in detection of phenolic group
  • c)
    Tollen reagent is used in detection ofunsaturation
  • d)
    Fehling solution is used in detection ofglucose
Correct answer is option 'C'. Can you explain this answer?

Priyanka Iyer answered
Tollen's reagent is used to detect of
aldehydes. Tollen's reagent is an ammonical
solution of silver nitrate. When aldehyde is
added to Tollen's reagent, silver oxide is
reduced to metallic silver which deposits as
mirror.

A strong base can abstract an α – hydrogen from
  • a)
    Alkane.
  • b)
    Amine
  • c)
    Ketone
  • d)
    Alkene
Correct answer is option 'C'. Can you explain this answer?

Vijay Bansal answered
After deprotonation the negative charge will be in conjugation with the pi orbital of carbonyl..so base will prefer to abstract alpha hydrogen from ketone.

In which of the following reactions, ketone is formed as the major organic product?
  • a)
  • b)
  • c)
  • d)
Correct answer is option 'A,C'. Can you explain this answer?

If acid derivatives like nitrile, acid chlorid e or ester is taken in excess in Grignard synthesis, second addition of Grignard’s reagent on carbonyl product does not succeed and carbonyls are obtained as major products.
In option (b), carboxylic acids and in option (d), an aldehyde is formed.

Which one of the following compounds will be most readily dehydrated?       [2010]
  • a)
  • b)
  • c)
  • d)
Correct answer is option 'D'. Can you explain this answer?

Raghav Khanna answered
The intermediate is carbocation which is
destabilised by C = O group (present on ��-
carbon to the –OH group) in the first three
cases. In (d), α–hydrogen is more acidic which
can be removed as water. Moreover, the
positive charge on the intermediate carbocation
is relatively away from the C = O group.
∴ Correct choice : (d)

Clemmensen reduction of a ketone is carried outin the presence of which of the following ? [2011]
  • a)
    Glycol with KOH
  • b)
    Zn-Hg with HCl
  • c)
    Li Al H4
  • d)
    H2 and Pt as catalyst
Correct answer is option 'B'. Can you explain this answer?



Clemmensen Reduction and Its Mechanism:

The Clemmensen reduction is a chemical reaction that involves the conversion of a carbonyl group in a ketone to a methylene group using zinc amalgam and hydrochloric acid. This process is particularly effective for reducing ketones to alkanes.

Role of Zn-Hg with HCl:

- In the Clemmensen reduction, zinc amalgam (Zn-Hg) serves as the reducing agent while hydrochloric acid (HCl) acts as a catalyst.
- The reaction occurs at high temperatures, typically refluxing conditions, to facilitate the reduction of the carbonyl group.
- The zinc amalgam reacts with the carbonyl group in the ketone, leading to the formation of an alkyl zinc intermediate.
- The alkyl zinc intermediate is unstable and undergoes protonation by HCl to form the corresponding alkane.

Comparison with Other Reagents:

- Glycol with KOH is commonly used for cleaving ethers, not for the Clemmensen reduction of ketones.
- LiAlH4 is a powerful reducing agent that can reduce ketones to alcohols, but it is not typically used in the Clemmensen reduction.
- H2 and Pt as a catalyst are commonly used for hydrogenation reactions, not for the Clemmensen reduction.

In conclusion, the Clemmensen reduction of a ketone is carried out in the presence of zinc amalgam and hydrochloric acid. These reagents work together to reduce the carbonyl group in the ketone to a methylene group, producing the desired alkane product.

In the above reaction product 'P' is       [2002]
  • a)
  • b)
  • c)
  • d)
Correct answer is option 'B'. Can you explain this answer?

Ishani Nambiar answered
Grignard reagent forms addition product with
bubbled carbondioxide which on hydrolysis
with HCl yields benzoic acid.

Which one of the following can be oxidised tothe corresponding carbonyl compound? [2004]
  • a)
    2-hydroxy-propane
  • b)
    Ortho-nitro-phenol
  • c)
    Phenol
  • d)
    2-methyl-2 hydroxy-propane
Correct answer is option 'A'. Can you explain this answer?

Bhavana Das answered
2-hydroxy-propane can be oxidized to the corresponding carbonyl compound
- Explanation:
- 2-hydroxy-propane: Also known as acetone, it has a hydroxyl group attached to a carbon atom. This hydroxyl group can be oxidized to a carbonyl group (C=O) through the process of dehydrogenation.
- Oxidation: Oxidation involves the loss of electrons or the gain of oxygen. In this case, the hydroxyl group in 2-hydroxy-propane can be oxidized to a carbonyl group by removing hydrogen atoms.
- Carbonyl compound: The resulting product after oxidation of 2-hydroxy-propane would be a carbonyl compound, specifically acetone. The carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom.
- Importance: The oxidation of alcohols to carbonyl compounds is an important reaction in organic chemistry as it allows for the conversion of one functional group to another, expanding the range of compounds that can be synthesized.
In conclusion, 2-hydroxy-propane can be oxidized to the corresponding carbonyl compound through the removal of hydrogen atoms from the hydroxyl group, resulting in the formation of acetone.

The OH group of an alcohol or the –COOH groupof a carboxylic acid can be replaced by–Cl using [2004]
  • a)
    phosphorus pentachloride
  • b)
    hypochlorous acid
  • c)
    chlorine
  • d)
    hydrochloric acid
Correct answer is option 'A'. Can you explain this answer?

Pragati Dey answered
Phosphorus Pentachloride as a Reagent for Substitution Reactions
Phosphorus pentachloride (PCl5) is commonly used as a reagent for substitution reactions involving the replacement of hydroxyl (-OH) groups with chlorine. This reaction is especially common in the conversion of alcohols to alkyl chlorides.

Mechanism of the Reaction
- In the presence of PCl5, the lone pairs on the oxygen atom of the alcohol or carboxylic acid attack the electrophilic phosphorus atom in PCl5.
- This leads to the formation of an intermediate complex which then undergoes elimination of HCl to form the desired alkyl chloride or acyl chloride product.

Advantages of Using Phosphorus Pentachloride
- Phosphorus pentachloride is a cost-effective and readily available reagent.
- It allows for a rapid and efficient conversion of alcohols and carboxylic acids to their corresponding chlorides.
- The reaction conditions are relatively mild compared to other chlorinating agents.

Alternative Reagents
- Hypochlorous acid (HOCl) is not a suitable reagent for this type of substitution reaction as it is more commonly used as a bleaching agent.
- Chlorine gas and hydrochloric acid are not typically used for the direct substitution of hydroxyl groups with chlorine due to the harsh reaction conditions and potential side reactions that may occur.
In conclusion, phosphorus pentachloride is the most suitable reagent for replacing the -OH group of an alcohol or the -COOH group of a carboxylic acid with chlorine due to its efficiency, mild reaction conditions, and availability.

Which of the following is correct? [2001]
  • a)
    Diastase is an enzyme
  • b)
    Acetophenone is an ether
  • c)
    Cycloheptane is an aromatic compound
  • d)
    All the above
Correct answer is option 'A'. Can you explain this answer?

Ruchi Chopra answered
Acetophenone is a ketone, cyclopentane
doesn’t contain (4n + 2)π electron hence is
not aromatic. Diastase is an enzyme used in
the preparation of Maltose (Malt sugar, C12
H22 O11) through hydrolysis of starch.

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