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Chemistry233Chapter3ProblemSet
1) Ineachmoleculebelow,circleandidentifythefunctionalgroups.
OHHN
H
H H
H
O
O
O
Durabolin is a commonly abused anabolic steroid. In addition to its illicit use, durabolin is also used medically for the treatment of osteoporosis in women.
Pseudoephedrine is present in many over-the-counter decongestants. Psuedoephedrine is becoming increasing less available because it is a common precursor for the illegal manufacture of methamphetamine.
O OH
O
O Aspirin is a common anti-inflammatory drug. It also has a blood-thinning effect and is used in the prevention of heart attacks.
NH
OS
Duloxetine (Cymbalta) is an antidepressant and mood stabilizing drug manufactured by Eli Lilly. Cymbalta reached $4.7 billion in sales in 2012.
N
O
N
Fentanyl is a narcotic analgesic administered in the form of a transdermal patch. Mylan Labs based in Morgantown was the first company to receive approval for generic production of fentanyl. Fentanyl is one of the best selling generic drugs in the world.
Chem.233–Chapter3ProblemSet
Page 2 of 4
2) DrawthefiveconstitutionalisomersforC6H14.
3) Determinethesystematic(IUPAC)nameforeachalkanecompoundbelow.
4) Drawthestructurethatcorrespondstoeachnamebelow.
5) Ineachcompoundbelowclassifytheindicatedcarbonasprimary,secondary,tertiary,quaternary,
ornoneoftheabove(NOA).
3,3-diethyl-4-methyl-5-propyloctane
3,6-diethyl-5-isopropylnonane6-ethyl-5-isopropyl-2,2,7-trimethyloctane
2,2,5-trimethylhexane
5-ethyl-4,4-dimethyloctane
3-methyl-4-propylheptane
2,2,6,8-tetramethyl-5-propylnonane3,7-diethyl-6-isopropyldecane
H H
CH4 (CH3)2CHCH2CH3
Chem.233–Chapter3ProblemSet
Page 3 of 4
6) Classifyeachalkylhalideoralcoholasprimary,secondary,tertiary,ornoneoftheabove(NOA).
7) DeterminetheIUPACnameforeachhalogen-containingcompoundbelow.Forthefirsttwo
structuresalsolistthecommonname.
8) Whichconformationineachpairishigherinenergy?Calculatetheenergydifferencebetweenthe
twoconformations.
OH Br I
ClH
OHBr H3C Br
F
ClBr
ClBr
Br
BrClF
2-bromo-4-tert-butyl-6-chloroheptane
2-bromopropane
4-bromo-2-ethyl-1-methylcycloheptane
6-bromo-4-tert-butyl-2,2-dimethylheptane 2-fluoro-1,1-
dimethylcyclopentane
1-chlorobutane
4-chloro-3-ethyl-2,6-dimethyloctane
These two are actually Ch 4 material
CH3
H CH3
CH3
HHCH3
H CH3
H
CH3Hor
H
CH3
CH3
CH3
HH
H
CH3
CH3
H
HH3C
or
Chem.233–Chapter3ProblemSet
Page 4 of 4
9) ConverteachstructuretoaNewmanprojectionaroundtheindicatedbond.
10) FocusingontheC2-C3bondof2,3-dimethylbutane,drawNewmanprojectionsforallpossiblestaggeredandeclipsedconformations.Rankthecompoundsinorderofincreasingstability.
11) FocusingontheC2-C3bondof3-methylpentane,drawNewmanprojectionsforallpossible
staggeredandeclipsedconformations.Rankthecompoundsinorderofincreasingstability.
H3C
CH3HO
HH
H
H H
Cl BrCH3H
H Cl
HH
H
H
HH
HH H
HH
HH
H
H
H
H
H
HH H
H
HHHH HH
H
H
A B C D E F A
Every Step is a 60° Rotation
CH3/CH3 gauche0.9 kcal/mol
H/H eclipse1.0 kcal/mol
H/CH3 eclipse1.4 kcal/mol
CH3/CH3 eclipse2.6 kcal/mol
Legend
E = 2.7 E = 6.2 E = 2.7 E = 5.4 E = 1.8 E = 5.4 E = 2.7 kcal/mol
H
HH
HHH
H
H
H HH
H
HH
HH
H
H
H H
H
H
HH
HHH
HH
HHH
HH
HH H
HH H
H
HA B C D E F A
Every Step is a 60° Rotation
CH3/CH3 or Et gauche~ 0.9 kcal/mol
H/H eclipse1.0 kcal/mol
H/C eclipse~ 1.4 kcal/mol
C/C eclipse~ 2.6 kcal/mol
Legend
E = 0.9 E = 5.0 E = 1.8 E = 5.0 E = 0.9 E = 4.2 E = 0.9 kcal/mol
Energy (Stability) Ranking:
A = E < C < F < B = D
Lowest EnergyMost Stable
Highest EnergyLeast Stable