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Chemistry234Chapter24-ProblemSet
1) Classifyeachamineasprimary,secondary,ortertiary.
2) GivetheIUPACnameforeachcompoundshownbelow.
3) Thestructureofpseudoephedrineisshownbelow.Showavalidreactionfortheconversionofpseudoephedrinetothehydrochloridesalt.Besuretoincludeboththerequiredreagent(s)andtheproduct.(3points)
NH
NH2N
NH
NH2Br N
N
ClNH N
H
HO
O
NH2N Br
N
O
Ph
OH
HN
Chem.234–Chapter24ProblemSet
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4) Theaminebelowcanbepreparedbyreducinganamide,anitrocompound,oranitrile.Showthestructureforeachofthesethreepotentialstartingmaterials.
5) Provideafullarrowpushingmechanismforthereactionshownbelow.Note:Youdonotneedtoshowanyarrowsforstep2(Ag2O,H2O).
6) Predictthemajorproductforeachreactionbelow.
NH2
amide nitro compound nitrile
NH
1. CH3I (xs)2. Ag2O, H2O
3. Heat+ N(CH3)3 + AgI + H2O
Ph NH2 +Ph
O NaBH3(CN)
MeOH
Ph NO2
H2
Pd/C
NH1. CH3I (xs)2. Ag2O, H2O3. Heat
NH2CH3I (xs)
NH2HBr
N 1. LAH2. H2O
Chem.234–Chapter24ProblemSet
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7) Rankthecompoundsineachsetbelowinorderofincreasingbasicity.
8) Showhowcyclohexylpropylaminecanbepreparedviareductiveaminationstartingwithammonia.Showthemechanismfortheoneofthereductiveaminationsteps.*Note:Orderdoesnotmatter.Youcanmakeeithercyclohexylamineorpropylaminefirst.
9) ShowhowbutylaminecanbepreparedviatheGabrielAmineSynthesis.
NH2
NH2
NH2
O
NH2 NH
NH
O
Chem.234–Chapter24ProblemSet
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10) ShowtheproductsfollowingaseriesoftwoHoffmaneliminationsofthecyclicaminebelow.
11) Rankthecompoundsbelowinorderofincreasingboilingpoint.
12) Writethecompleteelectronpushingmechanismforthereductiveaminationofbenzaldehydeandmethylamine.
NH
NH2NH2N