Sp09FinalQues - NAME(Print SIGNATURE Chemistry 310N Dr...

Chemistry 310N
Dr. Brent Iverson
Final
May 18, 2009
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

Honor Code
The core values of the University of Texas at Austin are learning, discovery, freedom,
leadership, individual opportunity, and responsibility. Each member of the University is
expected to uphold these values through integrity, honesty, trust, fairness, and respect
toward peers and community.
(Your signature)

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
! -Dicarbonyls
! -Ketoesters
! -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
C
O
R
-0.5
Protonated Amide
N H
3

Signature_________________________
2. (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.
3. (8 pts) On the left is drawn the Lewis structure of a simple amide. Draw the two next most important
contributing structures in the spaces provided. Be sure to show all lone pairs and formal charges. Place
arrows on the two structures on the left to indicate how you are moving electrons to create the structure
immediately to their right.
H
C H
H
C
O
N
H
H
3. (10 pts) Because of pi delocalilzation,many of the atoms in the molecules below are predicted to be in
the same plane. On the structures below, circle all the atoms that you believe will be located the same
plane at equilibrium. Do not circle atoms that are in the same plane only temporarily as their bonds are
rotating freely at room temperature.
1.