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All questions of Carboxylic Acids and Derivatives for Grade 12 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.

The correct IUPAC name of the folllowing compound is
  • a)
    5,6-Diethyl-8-methyl dec-6-ene
  • b)
    5,7-Diethyl-3-methyl dec-4-ene
  • c)
    5,6-Diethyl-3-methyl dec-4-ene
  • d)
    2,4,5-Triethylnon-3-ene
Correct answer is option 'C'. Can you explain this answer?

Gunjan Lakhani answered
The IUPAC name of the given compound is 5, 6 - diethyl -2- methyldec - 4 - ene. 
The parent hydrocarbon contains 10 carbon atoms and a double bond. 
It is called dec-4-ene.
One methyl group is present on second carbon atom and two ethyl groups are present on fifth and sixth carbon atoms.

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.

Identify the pair of enantiomers amongst the given pairs:
  • a)
  • b)
  • c)
  • d)
Correct answer is option 'B'. Can you explain this answer?

Nandini Iyer answered
The correct answer is Option B.
The 1st option has R configuration and 2nd has S configuration hence they are non super imposable mirror images of each other and are enantiomers.

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.

IUPAC name of compound
  • a)
    3-Bromo7-chloro-7ethyl-5-(1,1-dimethyethyl)-5-(2-methylpropyl)-3-methylnonane
  • b)
    3-Bromo7-chloro-5-(1,1-dimethyethyl)-7-ethyl-3methyl-5-(2-methylpropyl)nonane
  • c)
    3-Bromo7-chloro-7ethyl-3-,methyl-5-(1,1-dimethyethyl)-5-(2-methylpropyl)nonane
  • d)
    3-Bromo-5-(1,1-dimethyethyl)-5-(2-methylpropyl)-7-chloro-7ethyl-5--3-methylnonane
Correct answer is option 'B'. Can you explain this answer?

The correct answer is option B
First of all, we should number the carbon atoms from right to left for the above molecule. According to IUPAC rule, we have to name the functional groups alphabetically. Hence, bromine which is attached to 3rd carbon is named as 3-bromo, chlorine which is attached to 7th carbon is named as 7-chloro and ethyl group which is also attached to 7th carbon is named as 7-ethyl. 5-(1,1-dimethyethyl) indicates that, 2 methyl groups are attached to the 1st carbon of ethyl group which is attached to the 5th carbon of the given molecule. 5-(2-methylpropyl) indicates that, a methyl group is attached to the 2nd carbon of propyl group which is attached to the 5th carbon of the given molecule. Finally, since the molecule has nine atoms and it is an alkane, the word nonane is added to the IUPAC name.
 

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.

How manyh assymmetric carbon atoms are present in
(i) 2-Dimethyl cyclohexane
(ii) 3-Methyl cyclopentene
(iii) 3-Methylcyclohexene
  • a)
    2,1,1
  • b)
    1,1,1
  • c)
    2,0.2
  • d)
    2,0,1
Correct answer is option 'A'. Can you explain this answer?

Aarya Khanna answered
Asymmetric carbon atoms are those carbon atoms which are attached to four different groups or atoms. These carbon atoms are also known as chiral centers.

(i) 2-Dimethyl cyclohexane:
- Cyclohexane has no asymmetric carbon atoms.
- When two methyl groups are attached to cyclohexane, it becomes 2,3-dimethyl cyclohexane.
- The carbon at position 2 is attached to two methyl groups and two hydrogen atoms. Therefore, it is not an asymmetric carbon atom.
- The carbon at position 3 is attached to one methyl group, one hydrogen atom, one methyl group, and one cyclohexane ring. Therefore, it is an asymmetric carbon atom.
- Hence, there is one asymmetric carbon atom in 2-dimethyl cyclohexane.

(ii) 3-Methyl cyclopentene:
- Cyclopentene has one asymmetric carbon atom.
- When a methyl group is attached to cyclopentene at position 3, it becomes 3-methyl cyclopentene.
- The carbon at position 3 is attached to one methyl group, one hydrogen atom, one double bond with carbon, and one cyclopentene ring. Therefore, it is an asymmetric carbon atom.
- Hence, there is one asymmetric carbon atom in 3-methyl cyclopentene.

(iii) 3-Methylcyclohexene:
- Cyclohexene has one asymmetric carbon atom.
- When a methyl group is attached to cyclohexene at position 3, it becomes 3-methylcyclohexene.
- The carbon at position 3 is attached to one methyl group, one hydrogen atom, one double bond with carbon, and one cyclohexene ring. Therefore, it is an asymmetric carbon atom.
- Hence, there is one asymmetric carbon atom in 3-methylcyclohexene.

Therefore, the correct answer is option 'A' (2,1,1) as there are 2 asymmetric carbon atoms in total, with 1 in 2-dimethyl cyclohexane, 1 in 3-methyl cyclopentene, and 1 in 3-methylcyclohexene.

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.

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