/

Name: 5\-ir~ A
Exam2
Chemistry 333
(Fall 2019)

Question 1 16 points

Question 2 20 points A
Question 3 14 points fl_
Question 4 12 points (L
Question 5 12 points 8
f(
Question 6 12 points --
Question 7 9 points 9
--

Free Points 5 points

];:
Total 100 points (ff:)
Extra credit +5 points 2-

•I think you should be more

explicit here in step two.'
 Chemistry 333
Exam2 Fall 2019

1) Identify the operative mechanism(s) AND draw the missing products or

reactants. Where appropriate show stereochemistry. If the reaction
0 0 0 forms multiple products, draw all reasonable products. If multiple
/V\ \ l 3

er~/~~
elimination products are formed, then label the major product.
s/s .'.:NZ. '.:t->t f.:i. E s/t,J
slw sNt ~t SNt.. NR J II
0

ll-)IS .5N1. 51" 2.. £;),_ Fl r"r'c1 0-Na+

V
W/u.) Nfl rJ{l ~I/ ~r,
A) solvent= CH 3OH
V
/

- circle operative i -r No.Cl

mechanisms

IA)/vJ
CH 3OH

Br
8) circle ALL operative i
mechanisms ' ~============
on/yproduct

0y
VV
-
+ N'!J
G
I

SN1 ~ E1 E2
Na

Br 1,
circle ALL operative
mechanisms

alkyl halide nucleophlle or base

C)

H KOt-Bu

B r p c H3 solvent = THF
H SN1 SN2 E1

D) i,

-2-
 Chemistry 333 Fall 2019
Exam2

+ l9 2) Chirality
--\- 4 a) Rank the groups on the chiral center from highest to lowest using the Cahn-
lngold-Prelog for assigning chiral centers.

put letters in the boxes

[@ >[@> lowest
highest

+L\- b) Circle ALL of the chiral centers that are (R). The numbers are the Cahn-lngold-
Prelog priorities from 1 (highest) to 4 (lowest)

3,;\''2
1
4
1,,y
3 4
2
1/\°'3
2 (i)
I p_ .,......;;.,, ..
.. ,6) G),.. ,, ~ 0 ~ 6:1
+ f
c) Circle all the chiral centers n Simvastatin , w~ch is prescribed fo~ reducing LDL
cholesterol levels.
HO

+ 7 d) From the six molecules below, list the letters for ALL the molecules that are:
chiral: AICls meso: _.;_B_______
+- /_
H,:~: 0
+S OH

NH2 OH
Q qd OH Br
0-Br

B C D E F
A

~I\ f,\\I, .

4 -3-
H:,
., 11 6
J D,CA\N
3 -\k Com~~ -h,v -¾,u__ -to How 1t13
YnQc~O.Y\ISY\1
~oL-h()()s ( druw c.v<ved °'v-rows :fur fnl\ er.e dit),
w/w

~o
C.\
0how \.,\ow

0 w¼ pY11c\\)ds ~V"\

c5
c~
SN 1..:

E1

0
\\
_:_/_ '--_ o;::;,. -_ ~-x~
=- 0

b-( + No.6r
/'
io~;(, ( ~@ &-~
1--tob~
Chemistry 333 Exam2 Fall 2019

~~..,,.._l'!>Nl.
er I\IWl'i "00.1
MNli. lt)
li!E.~011~~!
If!. ,,_
1t£Ulo~.

4) For each of the following series, identify the most stable and least stable1 _ 3o
molecule by putting their corresponding letters in the boxes. C1A

CXf 0CXY w CXY Cs]

(±)

most least
stable
A B C D stable
a)

H
H CH 3
H~H ~~1!Ha H~CH3
HaC~ H CHa
HaC HH H CH3
CH 3 HCH3 CH3
most least
A B C D stable stable
b)

6- c:!z__ [l 0 least
most
A B C D stable stable
c)

CX' C(' er ex 0 @]
most least
A B C D stable stable
d)

-5-
Chemistry 333 Exam2 Fall 2019

5) Circle ALL the classifications that describe the relationship between the
following molecules.
OH
OH

A
~,,6
B C D E

A B C D E e
Which molecule(s} are enantiomers of A? (circle all that apply)

t')__ b} Which molecule(s} are stereoisomers of E? (circle all that apply) D,OS · .g;b b')o..~.

A 000 E none

0
J c} Which molecule(s) are constitutional isomers of C? (circle all that apply)

B C D E none

DEe
d) Which molecule(s) are the same molecule as D? (circle all that apply)

A0C
6) +(( Substitution and elimination

A) Which alkyl halide will react faster in an SN2 reaction? (Circle one)

Theywlll
all be the
Br Br Br Cl same

ls) Which nucleophile will react the fastest in an SN1 reaction? (Circle one)
(Ignore the possibility of elimination)

CH3CO~

-6-
 Chemistry 333 Exam2 Fall 2019

C) Ci~cle the reaction coordinate diagram that best describes a two-step

reaction where the second step is the slowest step.

~u ·,n ·.u 1~·-c 1111_.._. ...

~4A
Dl'I~

D) How many different E1 elimination products are possible for the reaction of

G
1-bromo-2,2-dimethylbutane with a strong base? (Do not count enantiomers.)

I '.__1_ 2 3 4
~) The reason that primary alkyl halides react faster than secondary alkyl
halides in SN2 reactions is because:
_/Primary alkyl halides are more crowded than secondary alkyl halides and

0.
eact faster with nucleophiles.
rimary alkyl halides are less crowded than secondary alkyl halides and
eact faster with nucleophiles.
_,,e(secondary carbocations are more stable than primary carbocations.
~primary carbocations are more stable than secondary carbocations.
e) primary alkyl halides do not react faster than secondary alkyl halides in
SN2 reactions.

+l F) The energy profile diagram below best represents the energy of rotation
around the carbons 2 and 3 of which of the following molecules? (Circle all
that apply)

ei
a,
ill

0° 60° 120° 180° 240° 300° 360°

-7-
Chemistry 333 Exam2 Fall 2019

7) f 1 True/False. If a statement is only partially true, then it is false.

J The half chair conformation of cyclohexane is higher in energy (less

stable) than the boat conformation.

A racemic mixture will have a different melting point and boiling point
than a sample of single enantiomer.

T Protic solvents speed up SN1 reactions by stabilizing the leaving

group.

f Doubling the concentration of an SN2 reaction will double the rate of

the reaction.

\ E2 eliminations must have a hydrogen on the beta-carbon that is on

the opposite side of the molecule from the leaving group.

f Hyperconjugation is the stabilization of a carbocation by adjacent

double bonds.

[ 9xtra credit (5 points).

'-t' l

areno;;~~;•glov;~~:~~
Name three chiral objects that fulfill the following criteria: They a r ' s - n D ~
The were not used as exa i cl ss, homework, or practice groblems, and they

1
/DNA 1
jfuy\S
vSeJ ·l\ ' vSeJ It s~
~'rt<!Mlt
+l Draw a mechanism (with curved arrows to show the bond breaking and making steps)
that explains the following transformation.
Hol,l -- ~o
Cl