Chemistry 22 Homework Set 6

1.(a) This example in proper format cla CI CI CH C12 94 HOW CI (m) Cop mixture (ep) unavoidable) (5) PL-CH3 NC now I'm usomy encourage, (as quared condensed format to to write this aut at ny sjuth and sayang to lotione at "ch yeah, I could have done that" - an Jaur first, then write aut what I'm degeribong honet Nitrate (p), reduce, diazotize (ine. 3-DEN), then CuCN (c) Ph-CH brommage (we need selectivity) AICI theme add the CI, F.R. Walaganate at the banaysets, Suz with C4,00, + then reduce the y=o to y Ta Clemnensen ar Alternatively, you wall-Kishner reductron. can halogenate the benzyse C forst, dispace with co, then F-C acfate, chlorinate the ring, & reduce. ↓ (a) Once I'll write the mechanisms, (2) no lists over the arrow, (3) no mechanisms, (4) no explanations, and (5) no mechanisms! NC Sucla C THPC 2 ay HI -NH2 C12(excess) CI Nitz NaNO CI N Y HI Fels CI CI I've included this key intermediate to help you follow the sequence- If I omit this, then I'll write: NANG H₃PO Hei 1. Nana, or HCI 2. H3PO2 T (or NABH) (a) Ph-CH3 HO CI nitrate (p), chlorinate, then oxidize the -CH3, reduce the rest to -NH2, diazotize with HONO (NaNO2, acid!) and couple the diazonium ion with an acid. or, you can synthesize the -NO2 for the -OH first(same sequence as described above), then oxidize the methyl.