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1.
Chemistry 11 Spring 2009 Examination #3 ANSWER KEY
® (46 pts. total)Tadalafil(sold under the trade nameCialis), is an orally administered prescription drug used to treat erectile dysfunction.
N H
alkene
O H
N
amide
CH 3 N
oO 2 amine ether (actually, an 'acetal', but will be formally noted in Section 4) O O Answer the questions below relating to this drug:
A.
B.
C.
D.
(4 pts.) Identify the functional groups labeled with arrows in the structure above. If any alcohols or amines are present, determine if they are primary, secondary, or tertiary.see above
(2 pts.) Circle one answer in each row so that your entire answer best describes the HNC bond angles inTadalafil:
a bit less than
60º
90º
exactly equal to
109.5º
a bit more than
120º
180º
(4 pts.) The molecular formula ofTadalafilisC22H19N3O4.
(2 pts.) Add, subtract, or otherwise change NO MORE THAN 3 ATOMS inTadalafilYouto create a new molecule that contains a carboxylic acid. may remove other functional groups if necessary.several possibilities here; consider the following: O H CH 3 N
N H
N
O
OH
O
carboxylic acid
E.
F.
Chemistry 11 Spring 2009 Examination #3 ANSWER KEY
(6 pts.) On the structure below, clearly label all the stereocenters (if any) present inTadalafilas eitherRorS. O H CH 3 N R N N HR
O
O
O
(8 pts.) Compare each molecule below withTadalafil(above). In the box below each molecule, write “identical”, “enantiomer”, “diastereomer”, or “none of these”. O O H H CH 3H C 3 N N
N H
O
N
O
O
Diastereomer
N H
O
H
N
Enantiomer
O
O
O
N
CH 3
H C 3
N
O
O
N
O
N H
Diastereomer
O H
O
O
N
O
Identical
N H
G.
P H
N H
H.
I.
Chemistry 11 Spring 2009 Examination #3 ANSWER KEY
(8 pts. total; 4 pts. each) For each of the following molecules below, circle whether you would expect it to have a HIGHER or LOWER boiling point thanTadalafil(shown above). Briefly explain your answer.
O
O
O H
N
O
O
O H
N
O
O
CH 3 N
CH 3 N
would have a (CIRCLE ONE) higherlower boiling point thanTadalafil.
EXPLANATION:The addition of the phosphorus atom (in place of nitrogen) removes the potential for hydrogen bonding interactions, thereby decreasing the boiling point.
would have a (CIRCLE ONE) higherlower boiling point thanTadalafil.
EXPLANATION:Aromatic compounds are very stable and require harsh conditions to break the C=C bonds. Removal of the aromatic nature of this molecule will more than likely decrease its overall boiling point, making it easier to vaporize the liquid.
(1 pt.) What is the maximum number of stereoisomers possible for2 Tadalafil?4 maximum possible stereoisomers2 =
(8 pts.) In pharmaceutical research, structural analogs of drugs are often made in order to see if they have similar biological properties. Below is a structural analog ofTadalafilcalledMolecule A. O H
O
O
O
NH 2 H
2.
3.
J.
Chemistry 11 Spring 2009 Examination #3 ANSWER KEY
In the boxes below, draw the most stable and least stable chair conformations ofMolecule A: C(O)NH 2 H(O)C C(O)H C(O)NH 2
O O O O Least Stable Most Stable (3 pts.) WriteTfor True orFfor false beside each statement below:
1)
2)
3)
__T__Tadalafilis an optically active compound that rotates plane polarized light.
__T__ Enantiomers ofTadalafilpossess identical melting and boiling points.
__F__ A racemic mixture is either dextrorotatory or levorotatory.
(10 pts.) Draw four constitutional isomers with the molecular formula C3H9N using bondline notation, and label any potential amines as primary, secondary, or tertiary.
o 1
NH 2
N H o 2
NH 2
o 1
N o 3
(18 pts. total; 3 pts. each)NOMENCLATURE! Use the appropriate IUPAC notation to name/draw each of the organic structures below:
A.
B.
4,4diethyl2heptyne
mdiiodobenzene I
I
4.
C.
D.
E.
F.
Chemistry 11 Spring 2009 Examination #3 ANSWER KEY
9
1
10
OH
1
trans1,3dimethylcyclohexane
1
5,7diethyl2,4dimethylnonane
7ethyl2,2,3,8tetramethyldecane
cis4ethyl4hexen3ol
6 (14 pts. total)REACTIONS AND MECHANISMS! Predict the MAJOR product(s) for the reactions listed below, and give the appropriate curved arrow notation where requested. Write NR if no reaction occurs.
A.
B.
(2 pts.) CHO H OH HO H O (O(g)+ 6H 6CO (g) +2g)2 2 H OH H OH CH OH 2 ( C H O ) (combustion no need to balance!) 6 12 6 (2 pts.)Figure It Out!
+ excess H (g) 2
Ru
E.
product
Br
(7 pts.) Arrange the following compounds in order of expected increasing boiling point, and briefly explain your ordering:
mechanism:
C.
mechanism:
H
(4 pts.)
+ excess Cl (g) 2
(2 pts.)
<
<
The boiling point of the branched alkane is the lowest because it is more compact, which reduces the amount of contact between the molecules. Cycloalkanes have higher boiling points than continuous chain alkanes due to restricted carboncarbon bond rotation, making the structures rigid.
<
H Br
<
5.
A.
(12 pts. total)SHORT ANSWERS!
NR
Chemistry 11 Spring 2009 Examination #3 ANSWER KEY
product
(4 pts.)
D.
+
OH 2
+ H
H SO 2 4
+ H O 2
HO
OH
OH 2
H
Br
Br
CH Cl 2 2
B.
Chemistry 11 Spring 2009 Examination #3 ANSWER KEY
(5 pts.) Determine whether the descriptions below refer toCaptopril, Ibuprofen, orThalidomideby writing the drug name on the lines provided.
Thalidomide teratogenic; responsible for abnormal birth defects
Captopril effective for the treatment of high blood pressure and congestive heart failure
Thalidomide found to be useful in the treatment of leprosy and may also be useful in the treatment of AIDS
Ibuprofen its Senantiomer is active as a pain and fever reliever
Thalidomide both enantiomers are active sedatives
