Question

6. Provide reasonable step-by-step mechanisms for the following reactions. Use arrows to indicate the movement of electrons. catalytic CH.CH (solvent) cat. NaOH, H-O (solvent) 1 equiv HBE CH2Cl2 (solvent) 1 equiv NaOCH 00..... + CH,OH . NaBr Br CH OH (solvent)

Answer 1

- BO CN-H N-H • ATH COH Intramdecular proton transfer takes place with a the help of HBX tor > Destroy El Proton abstraction takes place by ott followed by e-shift to produce final aromatic compound i. e, pherol. - > O H + H Crhy-Chat Br- CH3-CH BY This is an example of nucleophile substitution reaction ivolving Logg - cleavage of ether using hydrobromie auid Her. Protonation of ether oxyger takes place followed by loss of ethyl carboration which results is formation of pherd and Bromo ethane. -> the count + (Hz-ök - Br This is also as enample of nucleophilic substitution of Br in by O-atom to form ether linkage. 03