Organic Elementary Chemistry CHEM 220 Exam 4 November 12, 2001 Dr. R.W. Nagorski
b |wxt ux t utw t atx |y {x tx |xx atxA f| T{ Vt Wx ;DKHLDLFC<
1) 2) 3) 4) 5) 6) 7) 8) 9) 10) 11) 12)
______/9 ______/9 ______/4 ______/6 ______/4 ______/2 ______/6 ______/3 ______/6 ______/9 ______/36 ______/6
Bonus ______/6 Total ______/100
Name:___________________ ID#:_____________________
CHEM 220 Exam 4 Page 2 November 12, 2001
Part A: Nomenclature
1) Give the IUPAC name for the structures shown below. (9 points)
a)
b)
I
c) NH2
2) Given the IUPAC names below; draw the structure for each compound. (9 points)
a) p-amino methyl benzene
b) 4-cyclohexyl-2-pentanamine
c) N,N-dimethyl-2-propanamine
CHEM 220 Exam 4 Page 3 November 12, 2001
Name:_______________________
Part B: Conceptual Problems
3) Draw all possible resonance structures for the ions shown below. (6 points)
a)
b)
4) Are the molecules below aromatic according to Huckels Rule? True or False. (8 points)
a) O
b)
c)
d)
CHEM 220 Exam 4 Page 4 November 12, 2001
5) Draw a resonance hybrid for each set of resonance structures and circle the most stable resonance structure. (4 points)
a)
b)
O
O-
O-
6) Why are tertiary radicals more stable than primary radicals? (2 points)
CHEM 220 Exam 4 Page 5 November 12, 2001
Name:_______________________
7) Rank the following alcohols from most acidic (1) to least acidic (5). (6 points)
OH OH
OH
O2N
NO2
OH OH O2 N NO2
NO2
NO2
8) Why is the nitrogen in compound A a moderately strong director ortho/para while the nitrogen in compound B is a strong ortho/para director. (3 points)
H N O A B H N
9) Indicate the most likely position of electrophilic aromatic substitution for the compounds below? (6 points)
CH3 OCH3
I OCH3 O
CHEM 220 Exam 4 Page 6 November 12, 2001
Part C: Reaction Mechanisms
10) Give the mechanism for the reaction shown below, showing all intermediates and the movement of electrons using arrows. (9 points) H O H H H H O AlCl3 CH3 + + HCl Cl CH3 H H H H H H
CHEM 220 Exam 4 Page 7 November 12, 2001
Name:_______________________
11) For the radical halogenation reaction shown below, name the three steps of the reaction and give one example of each step.
Br2 h Br + HBr
CHEM 220 Exam 4 Page 8 November 12, 2001
Part D: Reactions
12) What is the major product or products for each of the following reactions shown below? When more than one product is expect...