AROMATIC COMPOUNDS CONTENTS EXERCISE - I EXERCISE - II EXRECISE - III EXRECISE - IV(A) EXRECISE - IV(B) ANSWER KEY Exercise -I Q1. + CHCl3 + KOH + B unexpected product What are A& B? Explain with mechanism. Q2. PhCH MgCl + MeCHO PhCH CHOH Me + A 2 2 Ais an isomer of the other product & undergoes the haloform reaction to give o-toluic acid. What isA? Suggest a mechanismfor its formation. Q3. 2, 4 dinitrophenyl diazonium ion couple with PhOMe whereas 2, 4, 6 compound couple with 2, 4, 6 trimethyl benzene. (mesitylene). Explain. Q4. If there is kinectic isotope effect what will happen when (a) C H & C D are allowed to react separately but under identical condition with E+. 6 6 6 6 (b) a 50 : 50 mixture of C6H6 & C6D6 is allowed to react with a limited amount of reagent. (c) Anisole & 4D anisole are allowed to react with E+ separately. Q5. What are A to D? EtOH H 1. NaH 2. MeI 1. NaOH 2. H 1. SOCl2 2. AlCl3 Q6. The following diacid undergo intramolecular Fridel Craft acylation with concentrated H2SO4 to give two products. Give their structures with proper mechanism. Q7. Mesitylene + HF + BF3 Give proper reasoning. Ayellow colored compound (A) where mesitylene : HF : BF =1 : 1 : 1. Q8. What is the attacking site of diazocoupling of (i) napthol (ii) napthol (iii) resorcinol. Q9. Account for the following facts (a) why PhNO2 acting as suitable solvent in Fridel Carft Alkylation. (b) The diazo coupling of phenol is carried out at pH = 9. (c) Biphenyl is more reactive than benzene towards EAS. Q10. The nitration of furan with acetyl nitrate proceeds via 2, 5 addition intermediate with the reagent. Suggest a plausible mechanism for this product formation. Q11. HClO4 Product. What type of reaction it is? Give proper mechanism. Q12. when reacts with N O2 BF4 two products & are formed with 44% & 56% respectively whereas when treated with N O2 BF4 only one product is formed as sole product. The structure of the products given as follows . Q13. Iodination of Phenol & 2, 4, 6 trideuterophenol when carried out separately KH/KD ratio is found to be 4. Explain. Q14. No reaction furan CH2O + What are A& B? What explanation can you give for unreactivity of furan w.r.t. reagents as comparedto 2 Me-furan & pyrrole. Q15. AcCl AlCl3 AcClAlCl3 B (disubstituted product) (monosubstituted product) What are A & B? Explain with reason. Q16. Kolbe Schmidt reaction if carried out in presence of soidum phenoxide product will be exclusively sodium ohydroxy benzoate whereas if reaction is carried out in presenceof K+ OPh–, salt of p acid becomes major product. Explain. Q17. Heating acetone with an excess of phenol in presence of HCl produces bisphenol A (C15H16O2) & reaction involved in its formation are similar to those involved in synthesis of DDT. Explain structure ofA with mechanism.