CHE 312 Organic Chemistry II
Instructor: Dr. James L. Lyle
Office:
NSM D-323
Phone:
(310) 243-3388, (310) 243-3376
e-mail:
jlyle@csudh.edu
Office hours: MW 9-10:00 am; TTh 12-1:00 pm; open door policy.
Text: Organic Chemistry, 6th Edition, Morrison & Boyd.
Study Guide for...
Model kit
1. Grading:
Traditional letter grades will be assigned. A = 100-93%, A- = 92-90%, B+ = 89-88, etc.
Daily exams
= 100
4 exams @100 pts = 400
final exam
= 100
600
2. Exams. No make up exams will be given.
3. Final exam. The final exam will be will be comprehensive.
4. Homework.
Homework is very important to doing well in this class and mastering organic chemistry.
Homework is not going to be collected, but it should be done on a regular basis.
Suggested problems are attached. Many of these problems are lengthy. You should be
selective in which ones you do. If you have any questions, see the instructor.
5. Office hours. The instructor is available at any time outside of class for questions,
etc. Do not hesitate to seek help if there is anything you do not understand!
6. Prerequisite. Completion of the first semester of Organic Chemistry, lecture and
laboratory. Corequisite is enrolment in CHE-313.
7. Academic Integrity. Please review the statement on Academic Integrity in your
University Catalog. Cheating will not be tolerated.
8. Course goals, objectives and requirements are covered in the rest of this syllabus.
9. Attendance is expected. Two of the daily exams scores will be dropped to allow for
unavoidable absences.
10. The schedule, homework, etc. can be found: http://chemistry.csudh.edu
CHE-312
meeting
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3.
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27.
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45.
TENTATIVE SCHEDULE
Spring '03
date
subject
1/27
1/29
2/3
2/5
2/10
2/12
2/17
2/19
2/24
2/26
3/3
3/5
3/10
3/12
3/17
3/19
3/24
3/26
3/31-4/4
4/7
4/9
4/14
4/16
4/21
4/23
4/28
4/30
5/5
5/7
5/12
5/14
TBA
Infrared Spectroscopy 17.1,17.3-17.7
Nucl. Mag. Resonance
17.9-17.13,17.22
Aldehydes & Ketones
text
18
no class
EXAM I
Carboxylic acids
19
Functional derivatives 19/20
Carbanions I
21
Carbanions II
Michael Addition
EXAM II
Amines, syntheses
25
27
Spring Break, no class
Amines, reactions
Phenols
Aryl halides
EXAM III
Molecular Orbitals
Polynuclear Aromatics
Heterocyclics
Carbohydrates
EXAM IV
FINAL EXAM
22
23
24
26
28
30
34
CHE-312
HOMEWORK ASSIGNMENTS
Athough homework is not required to be turned in, it is required that you do it. You will
not pass this course if you do not conscientiously do the homework assignments. Some
of the following problems have multiple parts. It may not be necessary to do every part,
but you should be able to do any homework problem, or problems similar to them, on the
exams. The answers are in the Study Guide and should be consulted. You should also do
the homework on a regular basis after every lecture. There is too much to do and learn if
you put it off. If you have any questions see the instructor.
Subject
Assignment
IR:
please note that in some later printings
Of the text the problems in this chapter
are off by .1; 17.2 (which starts What
is... ) may be 17.3 in your text,
17.3 (which starts give the... ) may be
17.4, etc., 17.5.
(Note: spectra are analyzed at the end of
the Study Guide.)
Handout.
nmr:
17.8(a-f),17.11,17.13,17.12,17.15,17.16,17.29,
p. 643: 1(a thru i).
aldehydes
& ketones
p. 701: 1,2, outline syntheses of each of the
compounds in problem 2 using as many methods as
possible for each from your choice of starting
materials.
p. 702: 3,4,5,18.16,6,10(a thru h).
p. 706: 30,32,33.
Outline all steps in the mechanisms for
nucleophilic addition and acid catalyzed nucleophilic addition. Which mechanisms go with
which reactions of aldehydes & ketones?
carboxylic
acids
p. 747: 1,2,3,4,6,7,13,15(a,b,c),27.
func. deriv.
p. 787: 1,2,3,4,5,6,7,20,21.
Outline all steps in the mechanisms for nucleophilic acyl substitution and acid catalyzed
nucleophilic acyl substitution for appropriate
reactions.
carbanions:
21.11(mechanisms), 21.18,p 817: 1,2,3,6, mechanism
for 6(a,d),25.1(a),25.8,25.10(a,b,c),25.16,
25.19(a-d),25.20(a-d),27.1,p.985: 2,3,7.
amines:
p.843: 1,2,22.5,22.6,3.
p.878: 1,2,4,5,9,7,11,12,29,30,32.
phenols:
p.913: 1,4,5,8,33.
aryl halides:
p. 968: 1,2,3,8.
Outline mechanisms for nucleophilic aromatic substitution (bimolecular) and the benzyne mechanism.
molecular
orbitals:
handout, 28.3,28.6,28.7,28.10.
heterocycles: know the names of common heterocycles.
p 1074: 1,2.
polynuclear
aromatics:
1. Reactions. Predict the structures and names of the products (if any) of naphthalene
with:
a) CrO3, acetic acid
b) O2,V2O5
c) Na,C2H5OH,reflux
d) Na,C5H11OH,reflux
e) H2,Ni,heat,pressure
f) HNO3,H2SO4
g) Br2
o
h) conc. H2SO4, 80
i) conc. H2SO4, 160o
j) acetyl chloride,AlCl3,CS2
k) acetyl chloride,AlCl3,C6H5NO2
l) succinic anhydride,AlCl3,C6H5NO2
2. Reactions. Predict the structures and names of the products of the reaction of:
anthracene with:
a) K2CrO7,H2SO4
b) Na,C2H5OH,reflux
c) Br2
phenanthrene with:
a) K2CrO7,H2SO4
b) Na,C5H11OH,reflux
c) Br2
d) Br2,FeBr3
3. Predict the products of nitration of the following compounds:
a) 1-methylnaphthalene
b) 2-methylnaphthalene
c) 1-nitronaphthalene
d) 2-nitronaphthalene
e) 1-naphthalenesulfonic acid
f) 2-naphthalenesulfonic acid
g) N-(1-naphthyl)acetamide
h) N-(2-naphthyl)acetamide
i) alpha-naphthol
j) beta-naphthol
4. Outline syntheses of the following from naphthalene:
a) alpha-naphthol
b) beta-naphthol
c) alpha-naphthylamine
d) beta-naphthylamine
e) 1-iodonaphthalene
f) 2-iodonaphthalene
g) 1-nitronaphthalene
h) 2-nitronaphthalene
i) alpha-naphthoic acid
j) beta-naphthoic acid
k) 4-(1-naphthyl)butanoic acid
l) alpha-naphthaldehyde
m) beta-naphthaldehyde
n) 1-phenylazo-2-naphthol
o) 4-amino-1-naphthol
p) 1-bromo-2-methoxynaphthalene
q) 1,5-diaminoanaphthalene
r) 4,8-dibromo-1,5-diiodonaphthalene
s) 5-nitro-2-naphthalenesulfonic acid
t) 1,2-diaminonaphthalene
u) 1,3-diaminonaphthalene
v) ortho-aminobenzoic acid
w) phenanthrene
x) anthracene
y) 9,10-anthroquinone
5. Haworth syntheses of the following starting with compounds with fewer rings:
a) 2-methylnaphthalene
b) 1-methylnaphthalene
c) 1,4-dimethylnaphthalene
d) 1,7-dimethylnaphthalene
e) 1,6-dimethylnaphthalene
f) 1,4,6-trimethylnaphthalene
g) 1-phenylnaphthalene
h) anthracene
i) phenanthrene
j) 9-methylanthracene
k) 2-methylanthracene
l) 9-methylphenanthrene
m) 4-methylphenanthrene
n) 1-methylphenanthrene
carbohydrates: define the following terms and give examples:
carbohydrate
monosaccharide, disaccharide,polysaccharide
aldose, ketose
pentose
reducing sugar
Tollen's reagent
Fehling's reagent
Benedict's solution
epimers
Ruff degradation
Kiliani-Fischer synthesis
D, L
glucoside
alpha-glucoside
beta-glucoside
anomers
Additional Homework for Molecular Orbital Chapter:
1. Electrocyclic reactions. Predict the products of the following electrocyclic reactions
showing the stereochemistry in the products. Is the motion conrotatory or disrotatory?

hv

hv
2. Cycloadditions. Predict the products of the cycloaddition reactions listed below and
then indicate if the reaction is allowed or forbidden by conservation of molecular orbital
symmetry and why or why not.
[4+2]
+
[2+2]
+

3. Does a [1,3] sigmatropic rearrangement of an alkyl group proceed with retention or
inversion of configuration? Show you reasoning using molecular orbitals.