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

Alcohols Phenols and Ethers question

2008 · Shift 2 · Q16
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. /Alcohols Phenols and Ethers
  5. /2008 · Shift 2 · Q16

Alcohols Phenols and Ethers question

2008 · Shift 2 · Q16

JEE AdvancedChemistryAlcohols Phenols and EthersMCQ+3 / −1
A tertiary alcohol H upon acid catalysed dehydration gives a product I. Ozonolysis of I leads to compounds J and K compound J upon reaction with KOHKOHKOH gives benzyl alcohol and a compound L, whereas K on reaction with KOHKOHKOH gives only M. IIT-JEE 2008 Paper 2 Offline Chemistry - Alcohols, Phenols and Ethers Question 8 English ComprehensionThe structure of compound I is :
  1. A
    IIT-JEE 2008 Paper 2 Offline Chemistry - Alcohols, Phenols and Ethers Question 8 English Option 1
  2. B
    IIT-JEE 2008 Paper 2 Offline Chemistry - Alcohols, Phenols and Ethers Question 8 English Option 2
  3. C
    IIT-JEE 2008 Paper 2 Offline Chemistry - Alcohols, Phenols and Ethers Question 8 English Option 3
  4. D
    IIT-JEE 2008 Paper 2 Offline Chemistry - Alcohols, Phenols and Ethers Question 8 English Option 4
View written solutionFree

Correct answer: A

The user wants me to solve a multi-step organic chemistry problem by identifying the structure of compound I. I will solve this by working backward from the products of the reactions.

Step 1: Analyze the reaction of compound J

Compound J reacts with KOHKOHKOH to give benzyl alcohol (C6H5CH2OHC_6H_5CH_2OHC6​H5​CH2​OH) and a compound L. This is a classic example of the Cannizzaro reaction. This reaction is characteristic of aldehydes that lack α-hydrogens. In the presence of a strong base (like KOHKOHKOH), one molecule of the aldehyde is reduced to an alcohol, and another is oxidized to the salt of a carboxylic acid.

Since the reduction product is benzyl alcohol, the aldehyde (J) must be benzaldehyde (C6H5CHOC_6H_5CHOC6​H5​CHO).

The full reaction is: 2C6H5CHO→conc. KOHC6H5CH2OH+C6H5COOK2 C_6H_5CHO \xrightarrow{\text{conc. } KOH} C_6H_5CH_2OH + C_6H_5COOK2C6​H5​CHOconc. KOH​C6​H5​CH2​OH+C6​H5​COOK So, we have identified:

  • J = Benzaldehyde (C6H5CHOC_6H_5CHOC6​H5​CHO)
  • Product = Benzyl alcohol
  • L = Potassium benzoate (C6H5COOKC_6H_5COOKC6​H5​COOK)

Step 2: Determine the structure of compound I from ozonolysis

Compound I undergoes ozonolysis (O3O_3O3​, followed by a workup with Zn/H2OZn/H_2OZn/H2​O) to produce compounds J and K. Ozonolysis cleaves a C=CC=CC=C double bond and forms two carbonyl (C=OC=OC=O) groups. To find the structure of the alkene I, we can reverse the process by taking the two carbonyl products (J and K) and joining their carbonyl carbons with a double bond.

We know J is benzaldehyde (C6H5CHOC_6H_5CHOC6​H5​CHO). This means one part of the alkene I must have the structure C6H5−CH=C_6H_5-CH=C6​H5​−CH=.

Step 3: Evaluate the options based on the structure of I

Let's perform a hypothetical ozonolysis on each of the given options to see which one yields benzaldehyde (J) as one of the products.

  • Option A: C6H5−CH=C(C6H5)2→1.O3  2.Zn,H2OC6H5CHO+(C6H5)2COC_6H_5-CH=C(C_6H_5)_2 \xrightarrow{1. O_3 \; 2. Zn, H_2O} C_6H_5CHO + (C_6H_5)_2COC6​H5​−CH=C(C6​H5​)2​1.O3​2.Zn,H2​O​C6​H5​CHO+(C6​H5​)2​CO This reaction gives benzaldehyde (J) and benzophenone (K). This fits our analysis. Let's check the other steps for consistency. Compound K is benzophenone. Benzophenone has no α-hydrogens but is a ketone, so it does not undergo the Cannizzaro reaction. The statement "K on reaction with KOHKOHKOH gives only M" is consistent with K being unreactive under these conditions, so M would be K itself. The contrast is that J gives two products, while K gives only one (itself).

  • Option B: (C6H5)2C=C(CH3)C6H5→1.O3  2.Zn,H2O(C6H5)2CO+C6H5C(O)CH3(C_6H_5)_2C=C(CH_3)C_6H_5 \xrightarrow{1. O_3 \; 2. Zn, H_2O} (C_6H_5)_2CO + C_6H_5C(O)CH_3(C6​H5​)2​C=C(CH3​)C6​H5​1.O3​2.Zn,H2​O​(C6​H5​)2​CO+C6​H5​C(O)CH3​ The products are benzophenone and acetophenone. Neither of these can be J (benzaldehyde). Thus, this option is incorrect.

  • Option C: C6H5−CH=CH−C6H5→1.O3  2.Zn,H2O2 C6H5CHOC_6H_5-CH=CH-C_6H_5 \xrightarrow{1. O_3 \; 2. Zn, H_2O} 2 \, C_6H_5CHOC6​H5​−CH=CH−C6​H5​1.O3​2.Zn,H2​O​2C6​H5​CHO This reaction gives two molecules of benzaldehyde. So, J and K would be identical. While this would satisfy the condition for J, the problem describes the reactions of J and K in a way that suggests they are different compounds ("J...gives...L, whereas K...gives only M"). This makes this option less plausible than A.

  • Option D: C6H5−C(CH3)=C(CH3)−C6H5→1.O3  2.Zn,H2O2 C6H5C(O)CH3C_6H_5-C(CH_3)=C(CH_3)-C_6H_5 \xrightarrow{1. O_3 \; 2. Zn, H_2O} 2 \, C_6H_5C(O)CH_3C6​H5​−C(CH3​)=C(CH3​)−C6​H5​1.O3​2.Zn,H2​O​2C6​H5​C(O)CH3​ The product is two molecules of acetophenone. This cannot be J. Thus, this option is incorrect.

Based on this analysis, Option A is the only one that is fully consistent with the ozonolysis and Cannizzaro reaction steps.

Step 4: Verify the formation of I from a tertiary alcohol H

The first step in the sequence is the acid-catalyzed dehydration of a tertiary alcohol H to form the alkene I. Let's check if the alkene from Option A, C6H5−CH=C(C6H5)2C_6H_5-CH=C(C_6H_5)_2C6​H5​−CH=C(C6​H5​)2​, can be formed from a tertiary alcohol.

Consider the tertiary alcohol 1,2,2-triphenylethanol: C6H5−CH2−C(OH)(C6H5)2C_6H_5-CH_2-C(OH)(C_6H_5)_2C6​H5​−CH2​−C(OH)(C6​H5​)2​. Upon treatment with acid (H+H^+H+), the -OH group is protonated and leaves as a water molecule, forming a stable tertiary carbocation: C6H5−CH2−C(OH)(C6H5)2→H+C6H5−CH2−C+(C6H5)2+H2OC_6H_5-CH_2-C(OH)(C_6H_5)_2 \xrightarrow{H^+} C_6H_5-CH_2-C^+(C_6H_5)_2 + H_2OC6​H5​−CH2​−C(OH)(C6​H5​)2​H+​C6​H5​−CH2​−C+(C6​H5​)2​+H2​O Elimination of a proton from the adjacent carbon (CH2CH_2CH2​) gives the desired alkene I: C6H5−CH2−C+(C6H5)2→−H+C6H5−CH=C(C6H5)2C_6H_5-CH_2-C^+(C_6H_5)_2 \xrightarrow{-H^+} C_6H_5-CH=C(C_6H_5)_2C6​H5​−CH2​−C+(C6​H5​)2​−H+​C6​H5​−CH=C(C6​H5​)2​ Since a suitable tertiary alcohol precursor (H) exists, this final condition is also met.

Conclusion

The structure of compound I that fits all the described reactions is given in Option A.

PreviousNext

More from Alcohols Phenols and Ethers

  • A tertiary alcohol H upon acid catalysed dehydration gives a product I. Ozonolysis of I leads to compounds J and K compound J upon reaction with KOH gives benzyl alcohol and a compound L, whereas K on reaction with KOH gives only M.… Includes diagram2008 · MCQ
  • The reaction sequence given below is carried out with 16 moles of X. The yield of the major product in each step is given below the product in parentheses. The amount (in grams) of S produced is ​. Use: Atomic mass… Includes diagram2025 · Numerical
  • The correct reaction/reaction sequence that would produce a dicarboxylic acid as the major product is :2025 · MCQ
  • For the reaction sequence given below, the correct statement(s) is(are) Includes diagram2025 · Multiple correct
  • Reaction of iso-propylbenzene with O2​ followed by the treatment with H3​O+ forms phenol and a by-product P. Reaction of P with 3 equivalents of Cl2​ gives compound Q…2024 · Multiple correct
  • Consider the following reaction scheme and choose the correct option(s) for the major products Q, R and S. Includes diagram2023 · Multiple correct
  • In the given reaction scheme, P is a phenyl alkyl ether, Q is an aromatic compound; R and S are the major products. The correct statement about S is : Includes diagram2023 · MCQ
  • An organic compound (C8​H{}_{10}O2)rotatesplane−porarisedlight.ItproducespinkcolorwithneutralFeCl_3$ solution. What is the total number of all the possible isomers for this compound?2020 · Numerical