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

Hydrocarbons question

2019 · Shift 2 · Q11
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. /Hydrocarbons
  5. /2019 · Shift 2 · Q11

Hydrocarbons question

2019 · Shift 2 · Q11

JEE AdvancedChemistryHydrocarbonsNumerical+3 / −1
Total number of hydroxyl groups present in a molecule of the major product P is .............. JEE Advanced 2019 Paper 2 Offline Chemistry - Hydrocarbons Question 27 English
Numerical answer
View written solutionFree

Correct answer: 6

Step-by-Step Solution:

  1. Analyze the Starting Material: The starting molecule is tris(3-isopropyl-5-methylphenyl)methane. This means a central carbon atom is bonded to a hydrogen and three identical substituted phenyl rings. Each phenyl ring has a methyl group (-CH3) and an isopropyl group (-CH(CH3)2) at positions meta to the point of attachment to the central carbon.

  2. Analyze the First Reaction: Oxidation with hot KMnO4

    • Hot, concentrated potassium permanganate (KMnO4) is a powerful oxidizing agent used to oxidize alkyl side chains on a benzene ring.
    • Any alkyl group with at least one benzylic hydrogen (a hydrogen on the carbon atom directly attached to the benzene ring) is oxidized to a carboxylic acid group (-COOH).
    • In our starting material, each of the three phenyl rings has two alkyl side chains:
      • A methyl group (-CH3): The benzylic carbon has 3 hydrogens. It will be oxidized to -COOH.
      • An isopropyl group (-CH(CH3)2): The benzylic carbon has 1 hydrogen. It will also be oxidized to -COOH.
    • Thus, for each of the three rings, both the methyl and isopropyl groups are converted to carboxylic acid groups. The central C-H group is sterically hindered and less likely to react, so we consider the oxidation of the side chains as the major reaction pathway.
    • The intermediate product formed is tris(3,5-dicarboxyphenyl)methane.
    • This intermediate molecule has 3 rings, each with 2 carboxylic acid groups. Total number of -COOH groups = 3 * 2 = 6.

    Structure after Step 1: CH(C6H3(COOH)2)3\text{CH(C}_6\text{H}_3\text{(COOH)}_2)_3CH(C6​H3​(COOH)2​)3​

  3. Analyze the Second Reaction: Reaction with SOCl2

    • Thionyl chloride (SOCl2) is a standard reagent for converting carboxylic acids (-COOH) into acid chlorides (-COCl).
    • All 6 carboxylic acid groups in the intermediate will be converted to acid chloride groups.
    • R-COOH + SOCl2 -> R-COCl + SO2 + HCl
    • The product formed is tris(3,5-bis(chlorocarbonyl)phenyl)methane.
    • This molecule contains 6 acid chloride (-COCl) groups.

    Structure after Step 2: CH(C6H3(COCl)2)3\text{CH(C}_6\text{H}_3\text{(COCl)}_2)_3CH(C6​H3​(COCl)2​)3​

  4. Analyze the Third Reaction: Reaction with CH3MgBr (excess) followed by H3O+

    • This is a Grignard reaction. Methylmagnesium bromide (CH3MgBr) is a strong nucleophile.
    • Acid chlorides react with two equivalents of a Grignard reagent to form a tertiary alcohol after acidic workup.
    • The reaction for each -COCl group proceeds as follows:
      1. Nucleophilic attack by CH3- on the carbonyl carbon of the acid chloride forms a ketone: R-COCl + CH3MgBr -> R-CO-CH3 + MgBrCl.
      2. The resulting ketone immediately reacts with a second molecule of CH3MgBr: R-CO-CH3 + CH3MgBr -> R-C(OMgBr)(CH3)2.
      3. Acidic workup (H3O+) protonates the alkoxide to form the tertiary alcohol: R-C(OMgBr)(CH3)2 + H3O+ -> R-C(OH)(CH3)2.
    • Since there are 6 -COCl groups in the molecule and CH3MgBr is used in excess, all 6 groups will undergo this transformation.
    • Each -COCl group is converted into a 2-hydroxyprop-2-yl group (-C(OH)(CH3)2).

    Structure of the Final Product P: CH(C6H3[C(OH)(CH3)2]2)3\text{CH(C}_6\text{H}_3\text{[C(OH)(CH}_3)_2]_2)_3CH(C6​H3​[C(OH)(CH3​)2​]2​)3​

  5. Count the Number of Hydroxyl Groups in Product P

    • The final product P contains 6 of the -C(OH)(CH3)2 groups.
    • Each of these groups contains one hydroxyl (-OH) group.
    • Therefore, the total number of hydroxyl groups in one molecule of the major product P is 6.

Final Answer: The total number of hydroxyl groups is 6.

PreviousNext

More from Hydrocarbons

  • Choose the correct option(s) that give(s) an aromatic compound as the major product.2019 · Multiple correct
  • Which of the following reactions produce(s) propane as a major product?2019 · Multiple correct
  • Among the following reaction(s), which gives(give) tert-butyl benzene as the major product is(are)2016 · Multiple correct
  • In the following reaction, the major product is Includes diagram2015 · Multiple correct
  • In the following reactions, the product S is Includes diagram2015 · Multiple correct
  • The major product U in the following reactions is Includes diagram2015 · Multiple correct
  • Schemes 1 and 2 describe sequential transformation of alkynes M and N. Consider only the major products formed in each step for both the schemes. The product X is Includes diagram2014 · MCQ
  • Schemes 1 and 2 describe sequential transformation of alkynes M and N. Consider only the major products formed in each step for both the schemes. The correct statement with respect to product Y is Includes diagram2014 · MCQ