JEE AdvancedChemistryHydrocarbonsNumerical+3 / −1
Total number of hydroxyl groups present in a molecule of the major product P is .............. 

Numerical answer
View written solutionFree
Correct answer: 6
Step-by-Step Solution:
-
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. -
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.
- A methyl group (
- Thus, for each of the three rings, both the methyl and isopropyl groups are converted to carboxylic acid groups. The central
C-Hgroup 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
-COOHgroups =3 * 2 = 6.
Structure after Step 1:
- Hot, concentrated potassium permanganate (
-
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:
- Thionyl chloride (
-
Analyze the Third Reaction: Reaction with
CH3MgBr(excess) followed byH3O+- 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
-COClgroup proceeds as follows:- Nucleophilic attack by
CH3-on the carbonyl carbon of the acid chloride forms a ketone:R-COCl + CH3MgBr -> R-CO-CH3 + MgBrCl. - The resulting ketone immediately reacts with a second molecule of
CH3MgBr:R-CO-CH3 + CH3MgBr -> R-C(OMgBr)(CH3)2. - Acidic workup (
H3O+) protonates the alkoxide to form the tertiary alcohol:R-C(OMgBr)(CH3)2 + H3O+ -> R-C(OH)(CH3)2.
- Nucleophilic attack by
- Since there are 6
-COClgroups in the molecule andCH3MgBris used in excess, all 6 groups will undergo this transformation. - Each
-COClgroup is converted into a 2-hydroxyprop-2-yl group (-C(OH)(CH3)2).
Structure of the Final Product P:
- This is a Grignard reaction. Methylmagnesium bromide (
-
Count the Number of Hydroxyl Groups in Product P
- The final product P contains 6 of the
-C(OH)(CH3)2groups. - 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.
- The final product P contains 6 of the
Final Answer: The total number of hydroxyl groups is 6.
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