Sp06FinalQues - NAME(Print SIGNAT URE Chemistry 310N Dr...

Chemistry 310N
Dr. Brent Iverson
Final
May 11, 2006
NAME (Print): _____________________________
SIGNATURE: _____________________________
Please Note: This test may be a bit long, but there is a reason. I would like to give you a lot
of little questions, so you can find ones you can answer and show me what you know, rather
than just a few questions that may be testing the one thing you forgot. I recommend you
look the exam over and answer the questions you are sure of first , then go back and try
to figure out the rest. Also make sure to look at the point totals on the questions as a
guide to help budget your time.
Note: You must have your answers written in
pen if you want a regrade!!!!
Please print the
first three letters
of your last name
in the three boxes
For synthesis problems GO FOR PARTIAL CREDIT EVEN IF YOU DO NOT KNOW
THE ENTIRE ANSWER!!!WRITE DOWN WHAT YOU DO KNOW IS IN THE
REACTION SEQUENCE SOMEWHERE. YOU WILL GET PARTIAL CREDIT IF IT IS
CORRECT

10
9
8
7
6
5
4
16
15
(30)
(33)
(20)
(32)
(21)
(30)
(20)
(19)
(35)
(35)
(21)
(22)
(17)
(10)
(23)
(21)
(389)
11
14
Total
T
Score
12
13
3
2
1
Page Points

CH
3
CH
2
- H
R
2
C C
H
H
H -N( i- C
3
H
7
)
2
RC C H
COR'
O
RC H
2
CR'
O
RC H
2
CH
O
RC H
2
CCl
O
RC H
2
RCH
2
O H
HO H
ROC
O
COR'
O
C H
2
RC
O
COR'
O
C H
2
RC
O
CR'
O
C H
2
H
4
N
CO- H
O
R
RCH
2
O H
2
H
3
O
H -Cl
10
51
-7
Compound
pK
a
3-5
15.7
16
18-20
11
23-25
18-20
13
15-19
40
Carboxylic acids
β -Dicarbonyls
β -Ketoesters
β -Diesters
Water
Alcohols
Acid chlorides
Aldehydes
Ketones
Esters
LDA
Alkanes
Terminal alkynes
25
Terminal alkenes
44
9.2
Ammonium ion
Hydronium ion
Hydrochloric acid
Protonated alcohol
-2
-1.7

Signature_________________________
Pg 1 _____________(30)
True False
2. (2 pt. each) Here are a number of statements regarding general aspects of organic chemistry. Do not
second guess yourself, this is not meant to be tricky! Check the appropriate box to indicate whether the
statement is true or false.
B. Resonance contributing structures generally are used to describe pi electron
delocalization.
A. Resonance contributing structures generally involve moving lone pairs and pi
bonds between atoms.
C. The exceptions to the VSEPR model we saw this semester involved pi electron
delocalization.
D. In
1
H-NMR, signals for H atoms attached to more electronegative atoms appear
closer to TMS than the signals for H atoms attached to less electronegative atoms.
E. A carbocation can be stabilized by either hyperconjugation or resonance.
F. In 1 H-NMR, spin-spin splitting is caused by induced electron density movement
that in turn induces small magnetic fields.
G. Enolates are great electrophiles
1. (14 points) Suppose a relative of yours is having an MRI. In no more than four sentences, explain to
them what is happening when they have the MRI scan. We will be looking for a minumum of 7 key
points here.
H. When a reaction is under kinetic control, the more stable product is the
predominant one (greater motive), while when a reaction is under thermodynamic
control the product that forms faster (better opportunity) is the predominant one.

Signature_________________________
Pg 2 _____________(33)
3. (8 points) For the following molecules, write the correct hybridization state of the atoms indicated
by the arrows.