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Aldehydes, Ketones and Carboxylic Acids

AIPMT 2010 (Prelims)MCQMediumNot asked in last 5 yrs+4−1
Ques. 1AIPMT 2010 (Prelims)

Among the given compounds, the most susceptible to nucleophilic attack at the carbonyl group is

  1. CH3COOCH3
  2. CH3CONH2
  3. CH3COOCOCH3
  4. CH3COCl

Answer

(4) CH3COCl

Solution

Reactivity of acyl compounds towards nucleophiles depends on how electron-deficient the carbonyl carbon is and on how good the leaving group is.

–Cl donates very little electron density to C=O by resonance (poor 2p–3p overlap) and withdraws strongly by –I effect; Cl- is also the best leaving group.

Order: CH3COCl > (CH3CO)2O > CH3COOCH3 > CH3CONH2

Acetyl chloride is the most susceptible to nucleophilic attack.

Answer: (4)

Keep practising — Aldehydes, Ketones and Carboxylic Acids

Ques. 2AIPMT 2009

Propionic acid with Br2/P yields a dibromo product. Its structure would be

  1. [figure]
  2. CH2(Br)-CH2-COBr
  3. [figure]
  4. CH2(Br)-CH(Br)-COOH
Ques. 3AIPMT 2008

A strong base can abstract an α-hydrogen from

  1. ketone
  2. alkane
  3. alkene
  4. amine
Ques. 4AIPMT 2008

The relative reactivities of acyl compounds towards nucleophilic substitution are in the order of

  1. Acid anhydride > Amide > Ester > Acyl chloride
  2. Acyl chloride > Ester > Acid anhydride > Amide
  3. Acyl chloride > Acid anhydride > Ester > Amide
  4. Ester > Acyl chloride > Amide > Acid anhydride.
Ques. 5AIPMT 2008

Acetophenone when reacted with a base, C2H5ONa, yields a stable compound which has the structure

  1. [figure]
  2. [figure]
  3. [figure]
  4. [figure]
Ques. 6AIPMT 2007

Reduction of aldehydes and ketones into hydrocarbons using zinc amalgam and conc. HCl is called

  1. Cope reduction
  2. Dow reduction
  3. Wolff-Kishner reduction
  4. Clemmensen reduction
Ques. 7AIPMT 2007

The product formed in Aldol condensation is

  1. a beta-hydroxy aldehyde or a beta-hydroxy ketone
  2. an alpha-hydroxy aldehyde or ketone
  3. an alpha, beta unsaturated ester
  4. a beta-hydroxy acid.
Ques. 8AIPMT 2007

Which one of the following on treatment with 50% aqueous sodium hydroxide yields the corresponding alcohol and acid?

  1. C6H5CHO
  2. CH3CH2CH2CHO
  3. CH3- O \|C-CH3
  4. C6H5CH2CHO
Ques. 9AIPMT 2007

Which of the following represents the correct order of the acidity in the given compounds ?

  1. FCH2COOH > CH3COOH > BrCH2COOH > ClCH2COOH
  2. BrCH2COOH > ClCH2COOH > FCH2COOH > CH3COOH
  3. FCH2COOH > ClCH2COOH > BrCH2COOH > CH3COOH
  4. CH3COOH > BrCH2COOH > ClCH2COOH > FCH2COOH
Ques. 10AIPMT 2006

A carbonyl compound reacts with hydrogen cyanide to form cyanohydrin which on hydrolysis forms a racemic mixture of α-hydroxy acid. The carbonyl compound is

  1. formaldehyde
  2. acetaldehyde
  3. acetone
  4. diethyl ketone
Ques. 11AIPMT 2006

Nucleophilic addition reaction will be most favoured in

  1. CH3CHO
  2. CH3-CH2-CH2- O \|C-CH3
  3. (CH3)2C=O
  4. CH3CH2CHO

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