Chemistry233
Chapter4ProblemSet
1) Determinethesystematic(IUPAC)nameforeachalkanecompoundbelow.
Br
F
F
Br
2) Drawthestructurethatcorrespondstoeachnamebelow.
1-butyl-3-ethyl-2-isopropylcycloheptane
1,1,2,2-tetramethylcyclopropane
cis-1,3-diisopropylcyclohexane
trans-1-ethyl-2-methylcyclobutane
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Chem.233–Chapter4ProblemSet
3) Drawtheringflippedconformationthenlabeleveryaxialandeveryequatorialpositiononboth.
4) Labeleachofthefollowingascisortrans.
OH
Cl
CH 3
Cl
Br
OH
5) Drawbothchairconformationsforeachofthefollowingcompounds.Circletheconformationthat
ismorestable.
cis-1,2-dimethylcyclohexane trans-1,2-dimethylcyclohexane
cis-1-bromo-3-methylcyclohexane
trans-1-isopropyl-3-methylcyclohexane
6) Forthecompoundshownbelow:(a)drawbothchairconformations,(b)determinewhichoneis
morestable,(c)determinetheconformationthat>95%ofthemoleculeswillbeinatequilibrium.
OH
Br
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Chem.233–Chapter4ProblemSet
7) Usingthechairbelowasatemplate,drawastructurethatmeetsthefollowingcriteria.
a) AxialmethylatC3,equatorialethylatC1
5
1
6
3
4
2
b) EquatorialmethylatC6andaxialOHatC4
5
1
6
3
4
2
c) EquatorialClgroupsatC1,C2,andC4
5
6
3
4
1
2
8) ChallengeProblem:DrawaNewmanprojectionaroundtheC1-C2bondofthemoststable
conformationofcis-1-ethyl-2-methylcyclohexane.
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