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An organic compound P having molecular formula $$C_6H_6O_3$$ gives ferric chloride test and does not have intramolecular hydrogen bond. The compound P reacts with 3 equivalents of $$NH_2OH$$ to produce oxime Q. Treatment of P with excess methyl iodide in the presence of KOH produces compound R as the major product. Reaction of R with excess iso-butylmagnesium bromide followed by treatment with $$H_3O^+$$ gives compound S as the major product.
The total number of methyl ($$-CH_3$$) group(s) in compound S is ______.
Correct Answer: 12
Step 1: Identification of Compound P
Consequently, compound $$P$$ is phloroglucinol ($$1,3,5$$-trihydroxybenzene). Phloroglucinol readily exhibits keto-enol tautomerism to exist in its keto form, cyclohexane-$$1,3,5$$-trione. Because it has $$3$$ carbonyl groups in this form, it reacts perfectly with $$3$$ equivalents of hydroxylamine ($$\text{NH}_2\text{OH}$$) to yield the trioxime Q.
Step 2: Formation of Compound R
When phloroglucinol ($$P$$) is treated with excess methyl iodide ($$\text{CH}_3\text{I}$$) in the presence of a strong base like $$\text{KOH}$$, it undergoes exhaustive C-alkylation at its active methylene positions rather than O-alkylation.
Each of the three $$-\text{CH}_2-$$ positions in the cyclohexane-$$1,3,5$$-trione tautomer is methylated twice, leading to $$2,2,4,4,6,6$$-hexamethylcyclohexane-$$1,3,5$$-trione as compound $$R$$.
Step 3: Formation of Compound S
Compound $$R$$ contains $$3$$ ketone carbonyl groups. When treated with excess iso-butylmagnesium bromide ($$\text{i-BuMgBr}$$, a Grignard reagent) followed by acid hydrolysis ($$\text{H}_3\text{O}^+$$), each carbonyl carbon undergoes a nucleophilic addition reaction to form a tertiary alcohol.
Step 4: Total Methyl Group Count in S
Let's add up all the methyl ($$-\text{CH}_3$$) groups present in the final structure $$S$$:
$$\text{Total number of methyl groups} = 6 + 6 = 12$$
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