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410 Chapter 21 AMINES AND THEIR DERIVATIVES: FUNCTIONAL GROUPS CONTAINING NITROGEN (b) Work backward. 0 CH₃ Excess HO CH₃ Internal SN2 H CH₃I H C₆H₅ H C₆H₅ C₆H₅ H CH₃ H N(CH₃)₃ H NHCH₃ + Ephedrine CH₃ Similarly H H H H C₆H₅ CH₃ C₆H₅ Pseudoephedrine Ephedrine and pseudoephedrine are diastereomers! 50. Analyze the Mannich reaction in terms of the functional unit it constructs. H 0 H + N-C-C-C- N C + C C NH + C + H-C-C- H H H H Relevant bonds are emphasized in the answers below. () 1. HCI 0 2. (a) CH₃CCH₃ + + HN(CH₂CH₃)₂ 1. HCI (b) 0 + + HN(CH₃)₂ H₂N-CH-CN + CH₃CHO + HCN (c) CH₃ Here the nucleophile is it is the cyanide ion that adds to the iminium carbon. () 1. HCI (d) CH₂CH₃ () + + HN(CH₃)₂ () 1. HCI () (e) 2. HO 2 + + CH₃ Two Mannich reactions are involved in this example. Note the primary amine and the presence of two moles each of formaldehyde and acetone.