Chemistry 233 Chapter 3 Problem Set
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Page 1 of 4 Chemistry 233 Chapter 3 Problem Set 1) In each molecule below, circle and identify the functional groups. OH H N 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. N H O S 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. alcohol mine arene are pester Keene ester ylic acid sulfide amine ether atone arene arene Answer Key
Transcript of Chemistry 233 Chapter 3 Problem Set
Page 1 of 4
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.
alcohol
mine
arene
arepester
Keene
ester
ylicacid
sulfideamineether
atone
arene
arene
Answer Key
Chem.233–Chapter3ProblemSet
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2) DrawthefiveconstitutionalisomersforC6H14.
3) Determinethesystematic(IUPAC)nameforeachalkanecompoundbelow.
4) Drawthestructurethatcorrespondstoeachnamebelow.
5) Ineachcompoundbelowclassifytheindicatedcarbonasprimary,secondary,tertiary,quaternary,
ornoneoftheabove(NOA).
2,2,6,8-tetramethyl-5-propylnonane3,7-diethyl-6-isopropyldecane
H H
CH4 (CH3)2CHCH2CH3
Becausethey are constitutionalisomers each will have a
µUnique IUPAC name
zl z 3 s
Z 3 y sby 4 s
bs 7
gas
isopropyl
gT
s 43 z G
Sc 3 G s 4 3 z
I
7 8 s9
Y V I I
MEET Texansj I 1
10 20 30 4020 NOA
cannotclassify
3doubleTtriplebonded
zo Carbonusingthis system
Bcs CILClbCBC H
40NOA NOA 30
Chem.233–Chapter3ProblemSet
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6) Classifyeachalkylhalideoralcoholasprimary,secondary,tertiary,ornoneoftheabove(NOA).
7) DeterminetheIUPACnameforeachhalogen-containingcompoundbelow.Forthefirsttwo
structuresalsolistthecommonname.
8) Whichconformationineachpairishigherinenergy?Calculatetheenergydifferencebetweenthe
twoconformations.
OH Br I
ClH
OHBr H3C Br
F
ClBr
Cl
Br BrClBrBr
Cl
F
CH3
H CH3
CH3
HHCH3
H CH3
H
CH3Hor
H
CH3
CH3
CH3
HH
H
CH3
CH3
H
HH3C
or
NOA
Talcohol 20bromide 30iodide
tobromide NOA methylbromide30alcohol C isnotattachedto 20chloride
anyotherC's
87
3 I4 3 e e I z 3 y SZ i z 3 sI Chlorobutane p l
Z f2bromopropane 3 chloro 4 fluoro2,24Chloro3ethyl2,6dimethyloctane dimethylpentane
1 z 3 y S
i 7 7 I2,2 dibromo 3methylpentane6bromo4 tertbutyl 2bromo 4 tertbutyl 6
2,2dimethylheptane chloroheptaseNumbering tie inbothdirectionsso Eromogets abc priority
sore in
k0.9 1,0 1.4 1.41,4
DE 1.80.9 0.9 DE 5.0 4.2 0.8
Chem.233–Chapter3ProblemSet
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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
HHgo I do I w
i ii130
Skew back skewfront
