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Chem 350
Fall 2016
Exam 2
‘There are 8 pages a pKa table and a periodic table in this exam
the staple
Multiple Choice
Page 6
Page 7
Page 8
Free response total
You have 90 minutes to complete this exam
You may use a scientific calculator and/or model kits on this exam
You may write on the back of the pages, but any material there WILL NOT be graded
In addition to putting your name on the front of the page, put your name on the back by
Be legible; if | cannot read your answer, it is wrong
* 140 points total
Substituent Avyalue (kcavmo}
oy CN 0.20
(# pts.) F 0.24
C=C oat
I 0.45
a 0.53
(18 pts.) Br 0.87
OH 0.93
NHe 1.41
(@ pts.) COM 1at
C=C 170
CH; 1.76
48 pts. CH.CHs 4.75
(sels) CH(CHs)o “iPr” 2.15
Ph 3.0
4 C(CH)s tBu" 5.0
Oo
& pts.) a
lalp = IamxcZ)
(am)xc(3)
@)pobserved
eee = [elo
[a]p pure sample
‘Chem350 — Exam 2 11)
BL
2)
E
Which of the following is/are identical of the boxed structure?
tonly
a
b. Ilonly ve N(CHg)o CH,CHs
c. Land Ilonly iH Hy
d. land Ill only CHACHs HN Nou cH, HN® N(CHsl2
e. Hand Ill only 1 Ww au
Rank the following in order of increasing acidity (least acidic to most acidic)
\ig. Weivclticl
b We en
# MWeilel Use the following energy diagrams to answer questions 3 to 5, assume all are drawn to scale
3)
4)
6)
reactor Teacton Teacton Teacion
conrdinate cooranste coordinate courdinats
Which one(s) represent(s) exothermic reactions?
tonly
2only
1 and 2 only
3 and 4 only
1,2, and 3 only
ese
Which one represents a reaction that is possibly too slow to occur even though it has a
negative AG°?
a. tonly
b. 2only
c. Sonly
led. 4 only
e. 2and3 only
Which one is the fastest reaction?
tonly
2only
only
4only
2and 3 only
eaocn
Given the following chair cyclohexane conformations, which one is more stable?
a. Ais more stable cl iPr
b. Bis more stable ipr ol
c. They are equal in energy NC: ie iPr
i
‘oH
by oN
A 8
‘Chem350 — Exam 27)
9)
B
11)
Ita sample is place
could notbe a reason?
The sample is achiral
There is more (A) enantiomer than (S) in the solution
The instrument is not plugged in
There is a racemic mixture
The sample is a meso compound
a polarimeter and no light rotation is observed, which of the following
gaegp
Rank the following in order of increasing acidity (least acidic to most acidic)
d. l