CHM 235
Prof. Robinson
Exam #2
Name
Summer 2005
ID#
Instructions:
 Answer any 10 of the following 11 questions.
 An 11th question may be answered for extra credit (also worth 10 points)
1. Name the five functional groups highlighted in the following compounds (2 pts each):
CH2NH2
O
O
C H
HOCCH2
CH2OH
CH3
2. (a) Show the products that will be formed in the acid base reaction between
CH3COOH (acetic acid) and Na+F-. (2 points)
CH3COOH + Na+F-
(b) Will products or reactants be favored at equilibrium if the pKa of CH3COOH is
4.76 and the pKA of HF is 3.45? ______________ (2 points)
(c) What products will be formed in the following Lewis acid/base reactions? Show
all lone pairs and include all non-zero formal charge in the products (3 pts each).
C
Cl
Al
+
CH3
N CH3
CH3
Cl
F
F
B
+
CH3 O CH3
F
1
3. (a) Using Newman projections, draw the three staggered conformations of 2methylbutane, looking down the C2-C3 bond. (5 points)
(b) Indicate how many gauche interactions there are in each conformation (3 pts)
(c) Circle the number of gauche interactions that will be highest in energy (2 pts)
Gauche
Interactions? _________
(Circle highest energy)
_________
________
4. Write the correct IUPAC name for the following molecule (10 pts):
CH2CH2CH2CH3
CHCH3
CH3CHCHCH2CHCH3
CH2CH3
CH2CH3
5. Write the correct IUPAC names for the following molecules (10 pts):
CH3
CH3
CH3
CH3CH2
CH3
CH3
CH3CH2CHCH2CHCH3
CH2CH2CH3
2
6. Draw condensed structures (such as CH3CH2CH3) for the following molecules:
 3-ethyl-2,4,5-trimethyloctane

cis-1,4-dibromocyclohexane

2,6-dimethyl-5-(1-methylethyl)nonane
7. Name the functional group in each of the following molecules.
O
CH3CH2CCH2CH3
CH3CH2 O CH2CH3
CH3CH2C OCH3
8. Convert the following Newman projection to:
a) the condensed structure (4 pts)
b) the stick or skeleton structure (3 pts)
c) name the molecule (3 pts)
H3C
C CH2CH3
CH2OH
O
H
HC
CH2CH3
CH3
H
H
3
9. a) Draw the most stable conformation of trans-1-tert-butyl-3-methylcyclohexane.
(Show the chair conformation and show substituents in the axial or equatorial positions)
b) Draw the most stable conformation of cis-1-tert-butyl-3-methylcyclohexane.
(Show the chair conformation and show substituents in the axial or equatorial positions)
10. Consider the following free radical halogenation reaction. Three different
monochlorination organic products are formed in this reaction. Give the condensed
structure for each organic product, and indicate how many different ways that
product can be formed.
CH3
light
CH3CH2 C CH2CH3
+
Cl2
three different
monochlorination products
+ HCl
CH3
Organic Product
Number of Ways Product Can Form
1)
2)
3)
4
11. The free radical halogenation reaction between 2-methylbutane and bromine gives
several different products, but the major product is 2-bromo-2-methylbutane. Show
how this product is formed by showing the initiation step, the propogation steps,
and the termination steps in the formation of this product.
CH3
CH3 C CH2CH3
+
Br2
light
H
CH3
CH3 C CH2CH3
Br
major product
Initiation step:
Propagation Steps:
Termination Steps:
5
+ HBr + other products