1) In each molecule below, circle and identify the...

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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

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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


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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

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


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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

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

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