Sign in
12thPass logo
New chatPYQ LibraryDoubtsRank report
Sign in to see Recents

Your guest activity stays on this device

Sign in to save progress →
Sign in

Aldehydes Ketones and Carboxylic Acids question

2018 · Shift 1 · Q17
Guest · filters and generic practice availableBrowsing as a guest · PYQ filters and generic practice are available. Sign in only for personalised features and saved progress.
  1. PYQ Library
  2. /JEE Advanced
  3. /Chemistry
  4. /Aldehydes Ketones and Carboxylic Acids
  5. /2018 · Shift 1 · Q17

Aldehydes Ketones and Carboxylic Acids question

2018 · Shift 1 · Q17

JEE AdvancedChemistryAldehydes Ketones and Carboxylic AcidsMCQ+3 / −0.75
An organic acid P (C11H12O2)\left( {{C_{11}}{H_{12}}{O_2}} \right)(C11​H12​O2​) can easily be oxidized to a dibasic acid which reacts with ethylene glycol to produce a polymer dacron. Upon ozonolysis, P gives an aliphatic ketone as one of the products. P undergoes the following reaction sequences to furnish R via Q. The compound P also undergoes another set of reactions to produce S. JEE Advanced 2018 Paper 1 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 69 English The compound R is
  1. A
    JEE Advanced 2018 Paper 1 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 69 English Option 1
  2. B
    JEE Advanced 2018 Paper 1 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 69 English Option 2
  3. C
    JEE Advanced 2018 Paper 1 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 69 English Option 3
  4. D
    JEE Advanced 2018 Paper 1 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 69 English Option 4
View written solutionFree

Correct answer: A

Step 1: Identification of Compound P

  1. Molecular Formula and Functional Group: The compound P has the molecular formula C11H12O2{C_{11}}{H_{12}}{O_2}C11​H12​O2​ and is an organic acid, which implies the presence of a carboxylic acid group (−COOH-COOH−COOH).

  2. Oxidation Product: P can be easily oxidized to a dibasic acid which reacts with ethylene glycol to produce the polymer dacron. Dacron is a polyester formed from the condensation of terephthalic acid (benzene-1,4-dicarboxylic acid) and ethylene glycol. This strongly indicates that the dibasic acid is terephthalic acid.

  3. Structure of P: Since P oxidizes to terephthalic acid, P must be a para-substituted benzoic acid. The structure can be represented as p−R−C6H4−COOHp-R-C_6H_4-COOHp−R−C6​H4​−COOH, where R is a side chain that can be oxidized to a −COOH-COOH−COOH group.

  4. Side Chain Formula: Let's determine the formula of the side chain R.

    • The formula of the p−C6H4−COOHp-C_6H_4-COOHp−C6​H4​−COOH part is C7H5O2C_7H_5O_2C7​H5​O2​.
    • Subtracting this from the molecular formula of P (C11H12O2{C_{11}}{H_{12}}{O_2}C11​H12​O2​): C11H12O2−C7H5O2=C4H7{C_{11}}{H_{12}}{O_2} - {C_7}{H_5}{O_2} = {C_4}{H_7}C11​H12​O2​−C7​H5​O2​=C4​H7​
    • So, the side chain R has the formula −C4H7-C_4H_7−C4​H7​.
  5. Degree of Unsaturation (DoU): For C11H12O2{C_{11}}{H_{12}}{O_2}C11​H12​O2​, the DoU is 11+1−122=611 + 1 - \frac{12}{2} = 611+1−212​=6. A benzene ring accounts for 4 DoU and the carbonyl group (C=OC=OC=O) in the carboxylic acid accounts for 1 DoU. This leaves 6−4−1=16 - 4 - 1 = 16−4−1=1 DoU for the side chain −C4H7-C_4H_7−C4​H7​, which means it must contain a double bond or a ring.

  6. Ozonolysis: The problem states that ozonolysis of P gives an aliphatic ketone as one of the products. Ozonolysis cleaves C=C double bonds. For an aliphatic ketone to be formed as a separate molecule, the structure of the side chain attached to the ring must be of the form −CH=C(R1)(R2)-CH=C(R_1)(R_2)−CH=C(R1​)(R2​). Ozonolysis (O3O_3O3​, then reductive workup with Zn/H2OZn/H_2OZn/H2​O) would yield p−(OHC)−C6H4−COOHp-(OHC)-C_6H_4-COOHp−(OHC)−C6​H4​−COOH and R1−CO−R2R_1-CO-R_2R1​−CO−R2​ (a ketone).

  7. Structure of the Side Chain: The side chain is −C4H7-C_4H_7−C4​H7​. We need to find R1R_1R1​ and R2R_2R2​ such that the total structure −CH=C(R1)(R2)-CH=C(R_1)(R_2)−CH=C(R1​)(R2​) has 4 carbons and 7 hydrogens. The ketone formed is R1−CO−R2R_1-CO-R_2R1​−CO−R2​. The simplest aliphatic ketone is acetone, (CH3)2CO(CH_3)_2CO(CH3​)2​CO. If the ketone is acetone, then R1=CH3R_1 = CH_3R1​=CH3​ and R2=CH3R_2 = CH_3R2​=CH3​.

    • Let's check the formula for the side chain −CH=C(CH3)2-CH=C(CH_3)_2−CH=C(CH3​)2​: It has 1+1+2=41+1+2 = 41+1+2=4 carbon atoms and 1+3+3=71+3+3 = 71+3+3=7 hydrogen atoms. The formula is −C4H7-C_4H_7−C4​H7​. This matches our requirement.
    • Thus, the side chain is the 2-methylprop-1-enyl group.
  8. Final Structure of P: Combining all the information, the structure of P is 4-(2-methylprop-1-enyl)benzoic acid.

P=HOOC−⟨◯⟩−CH=C(CH3)2P = HOOC - \langle \bigcirc \rangle - CH=C(CH_3)_2P=HOOC−⟨◯⟩−CH=C(CH3​)2​

Step 2: Reaction Sequence to form R

  1. P to intermediate: P reacts with thionyl chloride (SOCl2SOCl_2SOCl2​). This reagent converts a carboxylic acid into an acid chloride.

HOOC−⟨◯⟩−CH=C(CH3)2→SOCl2Cl−CO−⟨◯⟩−CH=C(CH3)2HOOC - \langle \bigcirc \rangle - CH=C(CH_3)_2 \xrightarrow{SOCl_2} Cl-CO - \langle \bigcirc \rangle - CH=C(CH_3)_2HOOC−⟨◯⟩−CH=C(CH3​)2​SOCl2​​Cl−CO−⟨◯⟩−CH=C(CH3​)2​

  1. Intermediate to Q: The resulting acid chloride undergoes Friedel-Crafts acylation with benzene in the presence of anhydrous AlCl3AlCl_3AlCl3​. The acyl group attaches to the benzene ring to form a ketone, Q.

Cl−CO−⟨◯⟩−CH=C(CH3)2+C6H6→Anhyd.AlCl3C6H5−CO−⟨◯⟩−CH=C(CH3)2Cl-CO - \langle \bigcirc \rangle - CH=C(CH_3)_2 + C_6H_6 \xrightarrow{Anhyd. AlCl_3} C_6H_5-CO - \langle \bigcirc \rangle - CH=C(CH_3)_2Cl−CO−⟨◯⟩−CH=C(CH3​)2​+C6​H6​Anhyd.AlCl3​​C6​H5​−CO−⟨◯⟩−CH=C(CH3​)2​ Structure of Q is (4-(2-methylprop-1-enyl)phenyl)(phenyl)methanone.

  1. Q to R: Compound Q is treated with H2H_2H2​ over a Palladium-Carbon catalyst (Pd−CPd-CPd−C). Catalytic hydrogenation reduces both the carbon-carbon double bond and the ketone group. The reduction of a diaryl ketone like this one under these conditions typically leads to the corresponding methylene group (CH2CH_2CH2​), a reaction known as hydrogenolysis.

    • Reduction of the C=C bond: −CH=C(CH3)2→−CH2−CH(CH3)2-CH=C(CH_3)_2 \rightarrow -CH_2-CH(CH_3)_2−CH=C(CH3​)2​→−CH2​−CH(CH3​)2​ (isobutyl group)
    • Reduction of the C=O group: −CO−→−CH2−-CO- \rightarrow -CH_2-−CO−→−CH2​− (methylene bridge)

    So, the final product R is:

C6H5−CH2−⟨◯⟩−CH2−CH(CH3)2C_6H_5-CH_2 - \langle \bigcirc \rangle - CH_2-CH(CH_3)_2C6​H5​−CH2​−⟨◯⟩−CH2​−CH(CH3​)2​

The name of this compound is 1-benzyl-4-isobutylbenzene.

Step 3: Comparison with Options

Let's examine the given options:

  • Option A: This structure matches our derived structure for R, which is 1-benzyl-4-isobutylbenzene.
  • Option B: The bridge between the two rings is CH(CH3)CH(CH_3)CH(CH3​), which is incorrect.
  • Option C: The isobutyl group is attached to the wrong benzene ring. The side chain was originally on the ring derived from benzoic acid.
  • Option D: The substituents are incorrect.

Therefore, the correct structure for compound R is given in option A.

PreviousNext

More from Aldehydes Ketones and Carboxylic Acids

  • Treatment of benzene with CO/HCl in the presence of anhydrous AlCl3​/CuCl followed by reaction with Ac2​O/NaOAc gives compound X as the major product. Compound X upon reaction with Br2​/Na2​CO3​, followed by heating…2018 · MCQ
  • Treatment of benzene with CO/HCl in the presence of anhydrous AlCl3​/CuCl followed by reaction with Ac2​O/NaOAc gives compound X as the major product. Compound X upon reaction with Br2​/Na2​CO3​, followed by heating…2018 · MCQ
  • In the following reaction sequence, the amount of D(in g) formed from 10 moles of acetophenone is ​. (Atomic weights in gmol−1:H=1,C=12,N=14,O=16,Br=80.. The yield (%) corresponding to the… Includes diagram2018 · Numerical
  • The desired product X can be prepared by reacting the major product of the reactions in LIST-I with one or more appropriate reagents in LIST-II (given, order of migratory aptitude: aryl > alkyl > hydrogen) The correct option is Includes diagram2018 · MCQ
  • Columns 1, 2 and 3 contain starting materials, reaction conditions, and type of reactions, respectively. The only CORRECT combination in which the reaction proceeds through radical mechanism is : Includes table2017 · MCQ
  • Columns 1, 2 and 3 contain starting materials, reaction conditions, and type of reactions, respectively. The only CORRECT combination that gives two different carboxylic acids is : Includes table2017 · MCQ
  • Columns 1, 2 and 3 contain starting materials, reaction conditions, and type of reactions, respectively. For the synthesis of benzoic acid, the only CORRECT combination is Includes table2017 · MCQ
  • The reaction of compound P with CH3​MgBr(excess) in (C2​H5​)2​O followed by addition of H2​O gives Q. The compound Q on treatment with H2​SO4​ at 0∘C gives R. The reaction of R… Includes diagram2017 · MCQ
The name of this compound is 1-benzyl-4-isobutylbenzene.