(Closed book, no models) Nov.

21 2017

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Name_______________________________________________________________
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First Middle initial
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Last 4 digits of Student's ID Number:______________
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Please circle the section you attend:
!
A01:!!!9%?/-7.!!
M 8:30 9:50(Kayla)
!!! ! ! A06: M 6:10 7:30 (Joseph)
9%?/-7.!! !!! ! A11:
!! T 2:10 3:30 (Joseph)
A02:!!!!"#$!!
M 4:40 6:00<#%-4!(Kayla)
! ! A07: W 6:10
"!#&! ! 7:30 (Jacob D)
'7(.! !!! A12:
! T 7:10
! 8:30! (Anoop)
!
A03: T 9:00 10:20 (Innes) A08: M 7:10 8:30 (Anoop) A13: R 6:10 7:30 (Anoop)
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1:40 3:00 (Jacob D)
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1) This
! exam consists of 5 pages (including this page) and 7 questions.
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2) After you are told to begin, please write the last 4 digits of your SID number on each page.
! have 50 minutes to complete the exam, please manage your time accordingly.
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4) Please
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5) You
50! must stop writing and turn in your exam when time is called.
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Fall 2017 118A Midterm 2 Page 2 of 5 Last 4 digits of ID________

1. (27 Pts) Multiple choice. Please choose one. Write your answers in the boxes at the bottom of the page.

a. Rank the following in order of increasing boiling point.

A) CH4< CH3F < CH3Cl < CH3Br < CH3I B) CH3F = CH3Cl = CH3Br = CH3I = CH4
A
C) CH3I < CH3Br < CH3Cl < CH3F < CH4 D) CH3-F < CH3-Cl < CH3-Br < CH3-I < CH3-H
b. Which of the following would increase the rate of the following reaction?
H 2O
(CH3)3CBr (CH3)3COH B
C) Using acetone as a solvent
A) Changing the leaving group to chloride D) Adding more water
B) Changing the leaving group to iodide E) B and C
c. A carbocation is hybridized.
B
A) sp3 B) sp2 C) sp D) unhybridized

d. Which of the following statements is true:

A) Compounds with only one stereocenter are only sometimes chiral
B) A molecule that contains a plane of symmetry is chiral
C) An enantiomer with the prefix D always rotates plane polarized light clockwise E
D) A compound with one stereocenter can be meso
E) A racemic mixture is optically inactive

e. How many total stereoisomers exist of 4-bromo-2-chloro-5-isopropyloctane? D

A) 1 B) 2 C) 4 D) 8 E) 9

f. Which of the following nucleophiles would lead to the fastest rate in a SN1 reaction in protic solvent?

A) NaI B) MeOH C) H2O D) NH3 E) All the same E

g. Rank the following in order of weakest to strongest nucleophile in an aprotic solvent

C
A) F- < Cl- < Br- < I- C) I- < Br- < Cl- < F-
B) F- = Cl- = Br- = I- D) F- = Cl- < Br- = I-

h. Which of the following substrates will undergo solvolysis in methanol

A) 1-chlorohexane B) 1-iodohexane C) fluoroethane D) 1-chloro-2,4-dimethylhexane E) None of the above

E

i. Which of the following groups has highest priority?

A) B) C) D)
CH2OH CH2CHO NHCH3 CH CHO C
CH3

Enter your answers for multiple choice questions in the boxes below:
a) b) c) d) E e) f) g) h) i)
A B B D E C E C

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Fall 2017 118A Midterm 2 Page 3 of 5 Last 4 digits of ID________

2. (14 pts) Assign the following molecules as chiral or achiral. Also assign the R, S to stereocenters.

CN OH

OHC Br H3CO

chiral 2 pts chiral 2 pts achiral 2 pts chiral 2 pts

R 2 pts S 2 pts S 2 pts

3. (16 pts) Determine if the following pairs of molecules are enantiomers, diastereomers, constitutional iosmers or
identical.
CH3 Br
constitutional iosmers
CH2OH
HO and H 3C
CH3 H
Br

CH3 Br
enantiomers
CN
NC and H 3C
H H
Br

Cl Cl identical
and

Cl Cl
diastereomers
F and

4. (8 Pts) Name the following molecule, include R/S stereochemistry where appropriate.

OMe 1 pts 1 pts 1 pt 1 pt 1 pts 2 pts

(4 ,6 ,7 )-3-ethyl-4-methoxy-6,7-dimethylnonane
1 pts

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Fall 2017 118A Midterm 2 Page 4 of 5 Last 4 digits of ID________
5. (16 Pts) Draw the structure of the expected organic product(s) formed in the following reactions including correct
stereochemistry. If the product is racemic, draw both enantiomers or write racemic next to the structure. If no
reactions occurs, write no reaction.

a.
(CH3)3OK
Br
(CH3)3OH CN
b. OSO2CH3
KCN -2 for stereochemistry

DMF

Br2 -2 for stereochemistry

h.
Br
hv Racemic

H 2O
d. No Reaction
I

6. (13 pts) Write the major organic product for the following reaction. Also show the detailed mechanism for thereaction.
Include electron arrows, relevant resonance structures, the structures of organic and non-organic products and
appropriate stereochemistry for all steps.
Br
CH3CH2OH
1 pt

Br or CH3CH2OH
1 pt H OCH2CH3
Br 1 pt OCH2CH3
1 pt 1 pt + HBr
Br + or CH3CH2OH2
1 pt 1 pt
1 pt 1 pt either of the two
3 pts
CH3CH2OH structures 1 pt

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Fall 2017 118A Midterm 2 Page 5 of 5 Last 4 digits of ID________

7. (6 pts) Cirlce the molecules(s) that could be the compound for this IR.

N
OH H O
N O O N
O O
O

N H
OH N
N
H O
O
O O
O

2 pts each for correct circles, -1 each for wrong circles

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