CHE-310 Organic Chemistry I
Instructor: Dr. James L. Lyle
Office: NSM-D-323
Phone: (310) 243-3388; 243-3376
Office Hours: Will be announced in class; open door policy
e-mail:
1. Grading:
Daily exams = 100
4 exams @ 100 pts = 400
final exam = 100
homework required
600
Letter grades will be assigned on the following basis. Grades are not curved.
A = 100-93%, A- = 92-90%, B+ = 89-87%, B = 86-83%, B- = 82-80%,
C+ = 79-77%, C = 76-73%, C- = 72-70%, D+ = 69-67%, D = 66-60%,
F = 59-0%
2. Required Texts:
Organic Chemistry, 6th Ed., Morrison & Boyd.
Study Guide for ...
Molecular Model Kit
Supplement...
3. Exams.
Daily exams will be given at the beginning of most lectures. No make up exams will be given, but the two lowest will be dropped. Attendance is expected. If you miss a daily exam it will count toward one of the two dropped exams. For scheduled hourly exams, no make up exams will be given. You must take the exams on the dates and times as scheduled.
4. Final exam.
The final exam will be comprehensive.
5. Homework.
Daily homework will be assigned. It is due at the beginning of the following lecture period. Penalty points will be assigned for missing or late homework.
6. Prerequisites.
The prerequisite for this course is completion of both semesters of General Chemistry. A corequisite is enrolment in CHE-311.
7. Office Hours.
The instructor is available at any time outside of class for questions, etc. Do not hesitate to seek help if you need it.
8. Cheating. Don't do it! At best you will receive a failing grade and be put on academic probation, at worst you will be expelled from the university. Review the University Catalog statement on Academic Integrity!
9. Course goals, objectives and requirements are covered in the rest of this syllabus.
CHE-310TENTATIVE SCHEDULEFall '02
MeetingDateChapt.Topic
1.8/26 1Introduction/Basic Principles
2.8/28 1Basic Principles
3.8/30 1Basic Prinicples
9/2no class
4.9/4 2Methane
5.9/6 2Methane
6.9/9 2Methane/Alkanes
7.9/11 3Alkanes
8.9/13 3Alkanes
9.9/16 3Alkanes
10.9/18*** EXAM I ***
11. 9/20 4Stereochemistry
12.9/23 4Stereochemistry
13.9/25 4Stereochemistry
14. 9/27 5Alkyl Halides
15.9/30 5 Alkyl Halides
16.10/2 5/7Alkyl Halides
17.10/4 6Alcohols
18.10/7 6Alcohols/Ethers
19.10/9 6Ethers
20.10/11*** EXAM II ***
21.10/14 8Alkenes, synthesis
22.10/16 8Alkenes, synthesis
23.10/18 9Alkenes, reactions
24.10/21 9Alkenes, reactions
25.10/23 9Alkenes, reactions
26.10/25 9Alkenes, reactions
27.10/28 10Stereochemistry
28.10/30 11Dienes
29.11/1 11Dienes
30.11/4 12 Alkynes
31.11/6*** EXAM III ***
32.11/8 13Alicyclics
33.11/11 13Alicyclics
34.11/13 13Epoxides
35.11/15 14Aromatic Hydrocarbons/Benzene
36.11/18 15Electrophilic Aromatic Substitution
37.11/20 15Electrophilic Aromatic Substitution
38.11/22 15Electrophilic Aromatic Substitution
39.11/25 16Arenes
40.12/27 16Arenes
11/29no class, Thanksgiving holiday
41.12/2 16Arenes
42.12/4*** EXAM IV ***
43.12/6TBA
44.TBA*** FINAL EXAM ***
CHEM-310 Information re Exam I
In studying for your first exam in this course, you should first go over all of the homework assignments and make sure that you understand them. In fact, you should be able to do any of the assigned homework problems on the exam. This is more difficult than doing the homework when you have access to your notes, etc. One way to prepare would be to redo all of your homework as if it were an exam. Then, pay particular attention to those problems that you cannot do or do not understand. If you have questions about any of the assigned material you should seek help immediately.
- be able to define important terms.
- from atomic numbers be able to give the numbers of protons and electrons in a neutral atom.
- be able to give spectral notations for neutral atoms.
- be able to identify ionic and covalent bonding.
- be able to draw Lewis dot structures for simple molecules.
- state the types of hybrid orbitals used in simple molecules and give their angles.
- know the relative strengths of some simple acids and bases.
- for acid base reactions, be able to predict if a reaction takes place, or if the reaction is given, label the stronger and weaker acids and bases.
- be able to predict which compounds are polar.
- predict the important products of the reactions of methane.
- be able to name alkanes.
- know the mechanism for free radical halogenation of alkanes. You may be asked to propose a similar mechanism for a reaction you have not done!
- be able to calculate enthalpy changes, given bond dissociation energies.
- be able to graph P.E. changes and label all parts of the graph.
- be able to estimate Energies of activation and predict which step in a mechanism is rate determining. Know the importance of Eact to the rates of chemical reactions.
- be able to draw hypothetical structures for transition states.
- understand the Hammond Postulate
- draw Newman projections for conformations in alkanes.
- be able to write equations to show how you would synthesize alkanes in the laboratory, given the starting materials.
- be able to predict the organic products of the reactions of alkanes.
CHE 310Information about Exam II
Your second exam will cover the chapters on stereochemistry, alkyl halides, alcohols and ethers. To study for this exam you should go over your homework assignments. It will also help to write your own version of the exam and trade with another student. Try to boil the subject down to the basic principles.
This exam will have a section on stereochemistry. You must be able to correctly specify R/S for stereoisomers (you may bring a model to the exam). You must know the definitions of the terms from this chapter, and understand what is important for each of the types of reactions of chiral molecules that you might encounter.
For alkyl halides, alcohols and ethers, be able to name compounds correctly (nomenclature). Where necessay, be able to specify congiguration in the name.
Know the two new mechanisms that we have learned in these chapters: SN2, SN1. Know which mechanisms go with which reactions under which conditions. Be able to write out all steps in the mechanisms for given reactions and label the RDS.
Be able to predict the organic products of the reactions of alkyl halides, alcohols and ethers. This is where you will be tested on the particulars of a reaction such as rearrangements, stereochemistry, and orientation.
Know how to synthesize any alkyl halide or ether from a given starting material. Some of the methods used in syntheses may also be covered in the part of the exam on reactions or mechanisms.
Pay particular attention to those homework problems that are of the above types. If you have any questions about the material, please do not hesistate to come see me.
J. Lyle
CHE 310 Homework # 1
1. Read Chapter 1 of your text.
2. Define the following terms: Organic chemistry, Pauli exclusion principle, Atomic orbital.
3. For each of the following, state how many protons are there in the nucleus? how many eletrons are there in shells about the nucleus? Give the spectral notation (1s22s2...): Na, Cl, Ne, Cl-, Na+, O, O2-, Br, Ar, Br-, I, C.
5. On page 5 of your text: 1.1 (a,b,c,d), 1.2 (a,b,c,d)
CHE 310 Homework # 2
1. Define the following terms: Ionic bond, Covalent bond.
2. What kind of hybridization is used by the central atom in each of the following compounds and what are the approximate bond angles?
CH4 BF3 BeCl2 NH4+ CH3+ (CH3)3B BF4-
3. Draw Lewis dot structures to show the bonding in the following covalent compounds:
NH3 H2O H3O+ NH4+ CO2
CHE-310Homework # 3
1. In your text do problems: 1.6 on page 26, 1.9 on page 35,
1.11 (a) page 36, 5 (a thru f).
2. In the following reactions, label the acids and bases involved, and label each as stronger or weaker.
H3O+ + HCO3- ----> H2CO3 + H2O
NaCN + H2O <---- HCN + NaOH
NaCl + HI ----> HCl + NaI
CH3MgBr + H2O ---> CH4 + Mg(OH)Br
3. Define the following terms:Lewis acid, Lewis base,Lowry-Bronsted acid,Lowry-Bronsted base,isomers.
CHE 310Homework # 4
1. Read Chapter 2
2. Predict the important products of the following reactions; if no reaction takes place, write N.R.:
A) CH4 + (xs)O2,flame ---->
B) 6CH4 + O2, 1500o ---->
C) CH4 + H2O, 850o,Ni---->
D) CH4 + Br2,hv ----->
E) CH4 + Cl2 ---->
F) CH4 + (xs)Cl2,heat ---->
3. Name the following compunds, giving two names for each:
CH3I CH2Br2 CHCl3 CBr4
4. Write all steps in the free radical substitution mechanism for the chlorination of methane. Label the initiating, propagating, and terminating steps. Label the rate determining step (RDS).
CHE 310Homework # 5
1. Calculate the enthalpy change (delta H) for the following reaction.
heat
CH4 + Br2 ------> HBr + CH3Br
2. Outline all steps in the mechanism for the above reaction, and calculate the delta H for each step in the mechanism.
3. Draw a graph of the potential energy changes in the second step of the above mechanism. (the graph can be free hand, but should have all parts labeled.)
4. Draw a graph of the P.E. changes in the third step of the mechanism.
5. An alternate mechanism for chlorination of methane was proposed by a student and contained the following two propagating steps:
(2) Cl. + CH4 ----> CH3Cl + H.
(3) H. + Cl2 ----> HCl + Cl.
Calculate the delta H for each of the above steps.
Why does the chlorination of methane proceed by the mechanism in the text and not by this alternative route?
CHE 310Homework # 6
The compound HOCl (hypochlorous acid) reacts with the compound C6H5CH3 (toluene) under the influence of ultraviolet light as shown in the following equation:
hv
C6H5CH3 + HOCl ------> C6H5CH2Cl + HOH
The bond dissociation energies pertinent to the above system are:
C6H5CH2-H 85; HO-Cl 60; C6H5CH2-Cl 68; H-OH 119 Kcal/mole
1. Calculate the enthalpy change for the reaction.
2. Write a stepwise mechanism for the above reaction and label the initiating and propagating steps. (Take the bond dissociation energy values into account when considering the most likely mechanistic steps.) Write two possible terminating steps.
3. Calculate the enthalpy changes for the steps in your mechanism, where possible.
4. Draw a graph of the potential energy changes for the third step in your mechanism. Label all parts of the graph.
5. Estimate the Energies of Activation for each of the propagating steps in the mechanism.
6. Which of the steps is the RDS (rate determining step)? How do you know?
7. Draw a hypothetical structure for the transition state for step 2 of the mechanism.
CHE-310Homework # 7
1. Read Chapter 3.
2. Draw the Newman Projections for the following conformations about the C2-C3 bond in n-butane: anti, gauche, CH3-H eclipsed, and CH3-CH3 eclipsed. Which of these are stable conformations?
3. Name the following structures:
CH3
CH3CH2CH2CH2CH3 CH3CH2CH2CH2
CH3 CH3 CH3
CH3CHCH2CHCH2CH3 CH3CH2CCH3
CH3
CH3 CH3
CH2 CH3 CH3 CH3 CH2
CH3CHCH2CH2CHCH3 CH3CH2CHCH2CHCHCH2CH2
CH2
CH2
CH3
4. Draw all nine isomeric heptanes (C7H16) and name each one.
CHE-310Homework # 8
page 99 3.9, 3.10,3.11
page 121 8, 9 (a,b,c)
CHE-310Homework # 9
1. In your text: p. 103:3.12;3.14 (predict the products and circle the major product. Do not predict the proportions.)
p. 121;10 (and circle the major product.)
2. Outline all steps in the mechanism for the bromination of ethane. Label the RDS.
CHE 310Homework # 10
1. Read Chapter 4.
2. Define the following terms: stereochemistry, optical acitivity, dextrorotatory, levorotatory, specific rotation, chirality, chiral center, enantiomers, racemic modification,configurations.
3. 4.3; 4.4; 4.5 (a-d); 4.8; 4.10 (a).
CHE-310Homework # 11(a)
1. Define the following: diasteromers, meso compound, resolution
2. In your text: 4.12 (a,b,h); 4.13.
CHE-310Homework # 11(b)
1. In your text: 4.24.
2. For each of the following reaction types, write a sentence or two to indicate the sterochemical importance of that type of reaction, or the basic principle to keep in mind about that type of reaction. a) a reaction of achiral compounds in which a chiral center is generated.
b) a reaction of a chiral compound in which no bonds to the chiral center are broken.
c) a reaction as in c) where a new chiral center is formed.
d) a reaction of a chiral molecule with an optically active reagent.
e) a reaction of a chiral molecule in which a bond to the chiral center is broken.
CHE-310Homework # 12
1. Read Chapter 5.
2. In your text: p. 211: 2; 3; 4;
3. Outline all steps in a possible laboratory synthesis of:
a) n-propyl bromide from n-propyl alcohol, TWO WAYS.
b) isopropyl iodide from isopropyl alcohol, THREE WAYS.
CHE 310Homework # 13
In your text:5.2;p. 212: 5; 6(a).
Predict the product(s) of the following reaction. You must show the stereochemistry of the product(s).
CH3
¦ SN2
H ---+--- Br + NaOH ----->
¦
CH2CH3
Using "curved arrow formalism", outline all steps in the mechanism for the following reaction and label the RDS.
CH3Br + NaOH -----> CH3OH + NaBr
Draw a hypothetical structure for the transition state of the RDS in the above mechanism. What is the name of this mechanism?
CHE 310Homework # 14
Predict the product(s) of the following reaction. Show the stereochemistry of the product(s):
CH3
¦ SN1
H ---+--- Br + NaOH ----->
¦
CH2CH3
Using "curved arrow formalism", outline all steps in the mechanism for the following reaction and label the RDS.
CH3 CH3
CH3C-Br + dilute NaOH -----> CH3C-OH + NaBr + alkene
CH3 CH3
Draw a hypothetical structure for the transition state of the RDS in the above mechanism. What is the name of this mechanism?
In your text: p. 212 8 (a-h); p. 271 4 (i,j);
CHE 310Homework # 15
page 245:1;6;
Complete the following reactions:
CH3
CH3CHCHCH3 + HBr ----->
OH
CH3CH2CH2CH2OH + HI ----->
p. 247 read "About Syntheses"
17 (a,b,d,e,h).
CHE-310Homework # 16
Outline all steps in the mechanism(s) for the reactions: Don;t forget to use "curved arrows" to show the movement of electron pairs. Label the RDS. Name each mechanism!
H+
CH3CH2-OH + HCl -----> CH3CH2-Cl + H2O
H+
tert-butyl alcohol + HBr -----> tert-butyl bromide + H2O
Give the structures of the organic products expected for the following reactions:
1. n-butyl alcohol with
a) sodium bromide, sulfuric acid
b) ethyl magnesium bromide (CH3CH2MgBr)
c) sodium bicarbonate (NaHCO3)
d) K2Cr2O7
e) C5H5NHCrO3Cl
f) CH3SO2Cl,OH-
g) acetic acid (CH3COOH),H+
2. sec-butyl alcohol with
a) P,I2
b) NaOH
c) Na
d) NaOCl (bleach)
e) CrO3
f) C6H5COOH,H+
3. tert-butyl alcohol with
a) HI
b) NaNH2
c) K
d) product of c) + ethyl iodide
e) KMnO4
f) Br2
CHE-310Homework # 17
page 245:2;3;7. Outline Williamson Syntheses for each of the ethers in problem 3.
CHE-310Homework # 18
In your text:8.1 (a) and name each compound (use E/Z for geometric isomers); 8.2; 8.5 and circle the major product if more than one is formed; 8.6 ( note: you want the alkyl halide that will give only one organic product from the dehydrohalogenation, not a mixture!);
p. 316:6 (a,b,c,e);7 (a,b,c,e).
Outline all steps in the mechanism for the following reaction. Label the RDS.
CH3CH2Br + KOH(alc) -----> CH2=CH2 + H2O + KBr
CHE 310Homework # 19
1. Predict the products of the following reactions. If more than one organic product is produced, circle the major product.
a) n-butyl bromide + KOH(alc) ---->
b) n-butyl alcohol + H+ ---->
c) neopentyl alcohol + H+ ---->
d) 2,3-dibromopentane + Zn ---->
2. Outline all steps in the mechanism for the following reaction. Label the RDS.
isopropyl alcohol + H+ ----> propylene
3. Why is dehydrohalogenation of an alkyl halide often preferred over dehydration of an alcohol in the synthesis of many alkenes?
4. p. 316: 13.
CHE-310Homework # 20
In your text:Page 363:1 (a-j);3 (a thru e);Page 366:
20 (a,b);21 (a).
Outline all steps in the mechanism for the following reaction: Label the RDS. Name the mechanism.
CH2=CH2 + HBr -----> CH3CH2Br
CHE-310Homework # 21
In your text:page 363:1 (k thru n);page 366:20 (c, d, e); 21 (b, c, d).
CHE-310Homework # 22
In your text:Page 363:1 (s,t);Page 363: 4.
Outline all steps in the mechanism of the following reaction: Label the RDS. Name of the mechanism?
H+
CH2=CH2 + H2O -----> CH3CH2-OH
Outline all steps in the mechanism for the following reaction: Label the RDS. Name of the mechanism?
perox.
CH2=CH2 + HBr -----> CH3CH2Br
CHE-310Homework # 23
In your text:page 363:1 (o thru r);16;17 (a);page 366:20 (f);21 (e,f).
CHE-310
Homework # 24
Define the following terms:stereospecific reaction, stereoselective reaction.
In your text:10.1;10.4.
CHE 310Homework # 25
1. Name the following compounds:
CH2=CH-CH=CH-CH=CH-CH3 CH3-CH=CH-CH2-CH=CH2
CH3
CH2=CH-C=CH2 CH3-CH2 H
\ /
C = C CH3
/ \ /
H C = C
/ \
H H
2. predict the product(s) of the following reactions:
CH3-CH=CH2 + Br2 ----->
heat
CH2=CH-CH3 + Br2 ----->
Homework # 26
1.. Give the structures of the organic products expected from the reaction (if any) of 1,3-butadiene with:
a) H2, Ni
b) 2 moles H2, Ni
c) Br2
d) 2 moles Br2
e) HCl
f) HBr, peroxides
g) KMnO4
h) Br2, H2O
2. Give the structures of the organic products expected from the reaction (if any) of 1,4-pentadiene with each of the reagents shown above in problem 1.
3. In your text: page 422 5 (b,f).
CHE 310Homework # 27
In your text: p. 441:1;2;4.
CHE 310Homework # 28
In your text:p. 488-489:1 (a,f,h);2 (a thru h);3 (b,h,j,k).
CHE 310Homework # 29
In your text:13.1;p. 488-489:1 (b,c,d,e);2 (i thru cc);3 (a,c thru f, i, j, k).
CHE 310Homework # 29-2
13.27; 13.25; p. 491: 16.
CHE 310Homework # 30
In your text:page 515-516:4 (a thru f) note the word theoretical; 9.
CHE 310Homework # 31
In your text:p. 515: 2 (d,e);p. 546: 1 (all).
CHE 310Homework # 32 (two days?)
In your text:p. 546: 2 (all); 3 (all);5.
p. 548: 15 (a - g);
Outline all steps in the mechanisms of the following reactions. Label the RDS.
a) nitration
b) sulfonation
c) halogenation
d) Friedel-Crafts alkylation
CHE 310Homework # 33
In your text:p. 581: 1 (all); 2 (a-h); 16.2
CHE 310Homework # 34
In your text:p. 581: 3 (all);p. 584: 18 (a,b,d,e);
p. 581: 4 (all).
CHE 310Homework # 35
In your text:
p. 581: problem 4 using phenylacetylene instead of trans-phenylpropene:(a,b,c,e,f,k,m,H2SO4 + Hg++ + H2O); 5 (all);
18 (c,g).
CHE 311 Sylabus
Instructor: Dr. J. L. Lyle
Office: NSM D-323
Phone: (310)243-3388;243-3376
Office Hours: Will be announced in class; open door policy
Required Texts:
Introduction to Organic Laboratory Techniques Pavia, Kriz, Lampman & Engel.
CRC Handbook of Chemistry and Physics (highly recommended)
Lab notebook
Safety goggles
1. Grading:Traditional letter grades will be assigned on the same basis as in CHE-310.
Lab reports 50%
Notebook 10%
Final Exam 25%
Evaluation 15%
2. Lab reports. A typed lab report will be required for each experiment. The report is due one week after the scheduled completion of the lab. These reports are due at the scheduled start time for the lab. Late reports will be penalized one letter grade for the first 24 hours. Lab reports that are submitted more than 24 hours late will not be accepted!
Please note that lab reports are not written in the lab notebook, but are separate requirements. You will be given explicit instructions about what each lab report is to contain. Lab reports are to be your own work and not plagiarised from some other student or lab report. Academic dishonesty will not be tolerated!
3. Notebook. A written record of what you are doing in the lab will be kept in your notebook. You are expected to have your notebook with you in the lab. Failure to do so can affect your grade. The notebook entries will be written in ink. The carbon copies that you make will be submitted with your lab reports.
4. Final Exam. A written final exam will be given at the end of the semester. Date and location will be announced later.
5. Evaluation. Part of your grade will be an evaluation of your lab technique, preparedness, punctuality, etc. by the instructor.
6. Safety. You must wear approved eye protection at all times in the lab. Failure to do so will result in expulsion from the lab.
7. Prerequisite. You must have completed both semesters of general chemistry. Corequisite is enrolment in CHE-310.
8. Attendance. You are expected to attend all laboratory sessions. Make ups will only be allowed if arrangements are made prior to the missed lab and for good reason.
9. Course goals, objectives, and requirements are covered elsewhere in this syllabus.
CHE 311Organic Chemistry Laboratory I
Week:
1.Check in/ Orientation to lab
2.Simple distillationP. 706-713