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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