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Aldehydes Ketones and Carboxylic Acids question

2017 · Shift 2 · Q3
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Aldehydes Ketones and Carboxylic Acids question

2017 · Shift 2 · Q3

JEE AdvancedChemistryAldehydes Ketones and Carboxylic AcidsMCQ+3 / −0.75
The reaction of compound PPP with CH3MgBrC{H_3}MgBrCH3​MgBr(excess) in (C2H5)2O{\left( {{C_2}{H_5}} \right)_2}O(C2​H5​)2​O followed by addition of H2O{H_2}OH2​O gives Q.Q.Q. The compound QQQ on treatment with H2SO4{H_2}S{O_4}H2​SO4​ at 0∘C{0^ \circ }C0∘C gives R.R.R. The reaction of RRR with CH3COClC{H_3}COClCH3​COCl in the presence of anhydrous AlCl3AlC{l_3}AlCl3​ in CH2Cl2C{H_2}C{l_2}CH2​Cl2​ followed by treatment with H2O{H_2}OH2​O producess compound S.S.S. [EtEtEt in compound PPP is ethyl group] JEE Advanced 2017 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 61 English ComprehensionThe product SSS is
  1. A
    JEE Advanced 2017 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 61 English Option 1
  2. B
    JEE Advanced 2017 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 61 English Option 2
  3. C
    JEE Advanced 2017 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 61 English Option 3
  4. D
    JEE Advanced 2017 Paper 2 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 61 English Option 4
View written solutionFree

Correct answer: A

  1. Identify compound PPP

    The statement says that in compound PPP, EtEtEt denotes an ethyl group. This standard question corresponds to an ester of benzoic acid, i.e. ethyl benzoate: P=C6H5COOEtP = C_6H_5COOEtP=C6​H5​COOEt

  2. Reaction of PPP with excess CH3MgBrCH_3MgBrCH3​MgBr followed by hydrolysis

    Esters react with excess Grignard reagent with two additions of the alkyl group.

    For ethyl benzoate: C6H5COOEt→ether2CH3MgBrC6H5C(OMgBr)(CH3)2→H2OC6H5C(OH)(CH3)2C_6H_5COOEt \xrightarrow[ether]{2CH_3MgBr} C_6H_5C(OMgBr)(CH_3)_2 \xrightarrow{H_2O} C_6H_5C(OH)(CH_3)_2C6​H5​COOEt2CH3​MgBrether​C6​H5​C(OMgBr)(CH3​)2​H2​O​C6​H5​C(OH)(CH3​)2​

    Hence, Q=C6H5C(OH)(CH3)2Q = C_6H_5C(OH)(CH_3)_2Q=C6​H5​C(OH)(CH3​)2​ which is 2-phenyl-2-propanol (cumyl alcohol), a tertiary alcohol.

  3. Treatment of QQQ with H2SO4H_2SO_4H2​SO4​ at 0∘C0^\circ C0∘C

    Tertiary benzylic alcohol undergoes dehydration readily to form the corresponding alkene: C6H5C(OH)(CH3)2→H2SO4C6H5C(CH3)=CH2C_6H_5C(OH)(CH_3)_2 \xrightarrow{H_2SO_4} C_6H_5C(CH_3)=CH_2C6​H5​C(OH)(CH3​)2​H2​SO4​​C6​H5​C(CH3​)=CH2​

    Therefore, R=α-methylstyrene=isopropenyl benzeneR = \alpha\text{-methylstyrene} = \text{isopropenyl benzene}R=α-methylstyrene=isopropenyl benzene

  4. Reaction of RRR with CH3COCl/AlCl3CH_3COCl/AlCl_3CH3​COCl/AlCl3​

    This is a Friedel–Crafts acylation. The substituent on benzene is: −C(CH3)=CH2-C(CH_3)=CH_2−C(CH3​)=CH2​

    This alkenyl side chain behaves like an alkyl-type activating group through hyperconjugative/electron-releasing effect and directs incoming electrophile to the ortho/para positions. Because of steric hindrance, the para product predominates.

    Thus acetyl group (−COCH3)(-COCH_3)(−COCH3​) enters mainly at the para position relative to the isopropenyl group.

    So, S=p-acetyl-α-methylstyreneS = p\text{-acetyl-}\alpha\text{-methylstyrene}S=p-acetyl-α-methylstyrene

    Structure: para-CH3CO-C6H4-C(CH3)=CH2\boxed{\text{para-}CH_3CO\text{-}C_6H_4\text{-}C(CH_3)=CH_2}para-CH3​CO-C6​H4​-C(CH3​)=CH2​​

  5. Matching with options

    The option corresponding to para-acetyl-α\alphaα-methylstyrene is Option A.


Final Answer

A\boxed{A}A​

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