Klutz McFingers. a graduate student in his ninth year of study, has suggested the following synthetic procedures and has come to you in the hope that you can explain why none of them works very well (or not at all).
(a) Noting the fact that primary alcohols + HBr give alkyl halides, Klutz has proposed by analogy the nitrile synthesis shown in part (a) of Fig. P21.50.
(b) Klutz has proposed the synthesis for the half-ester of adipic acid shown in part (b) of Fig. P21.50.
(c) Klutz has proposed the synthesis of acetic benzoic anhydride shown in part (c) of Fig. P21.50.
(d) Noting correctly that methyl benzoate is completely saponified by one molar equivalent of NaOH, Klutz has suggested that methyl salicylate should also undergo saponification with one equivalent of NaOH. (See structure in part (d) of Fig. P21.50.)
(e) Klutz, finally able to secure a position with a pharmaceutical company working on β-lactam antibiotics, has proposed the reaction given in part (e) of Fig. P21.50 for deamidation of a cephalosporin derivative.

Transcribed Image Text:

H2O Hin: HCN is a weak acid: its pK, is 94.) (1.0 mole) (1.0 mole) OH C OCH methyl salicylate HC-C NH H3N O-C-CH CH,CO H CO.H CO H Figure P21.50