Textbook and Materials
What you must buy
:
“Organic Chemistry” 4 th Ed. Janice G. Smith, McGraw Hill. (Older edition is fine)
“Chem 7A and 7B Lab Manual – Version 3” Robert Keil and Steve Joiner (bookstore)
Subscription to TWO online services: smartworks.com
(free), tophat.com
($20)
You should buy:
A lab coat and safety goggles. (Otherwise you’ll be using a loaner)
Getting in the Class
Instructors have little control over who gets added to classes, or whether they can add extra students. If someone is not in attendance in the first lecture or lab, and have not written me beforehand,
I drop them. The computer adds the next person on the waitlist. I have no control over who that is.
If you are not on the waitlist, your chances of getting in are very low. If no one has dropped after the first day of lab, it is highly unlikely that any space will open up. I cannot get any more add codes, I cannot let you audit in case a spot opens up, there is no method to allow me to choose who gets in the class. I will give out add codes as they become available in the third week of class.
Lecture Grade:
Exams: Four each at
100 points = 400 points ~50%
Weekly Homework: 5 points each =
Daily Quizzes 1-2 pts/day
Cumulative Final Exam
Lab Grade:
Pre-lab Quiz: 3-4 pts/day
Lab Sheet: 3-4 pts/day
Write-ups and Formal labs
Lab competency
=
=
75 points
60 points
(Norton SmartWorks)
(Top Hat)
100
= 60 points
=
20
(Top Hat ) points
=
15 points
(my assessment)
~
~
10%
8%
~8%
~3%
~2%
~13%
90% for an A; 80% for a B; 65% for a C; and 55% for a D.
All exams will be cumulative
. That is, anything you’ve covered in the past can be brought back at any time. Obviously, each exam will mostly cover new material, but you cannot forget what you’ve covered!
There is no “curve” in this course. Everyone can earn an A or everyone can fail. You are not competing against your neighbor! No extra credit is offered.
You must attend and complete the lab portion of the class, even if you are repeating the course or have taken a lab class at another school.

Office Hours
My office is in PS-126. Office hours are before and after lecture Monday and Weds. I will be in
(and out) on my office Tuesday 8:30 am-noon and some Thursdays.
Email at rkeil@vcccd.edu
(best); phone 805-378-1400 xtn 1765
Attendance and Dropping the Class:
If you miss more than two weeks of class (or more than one exam), you will not pass!
It is your responsibility to drop and make sure you are dropped.
Pre-Requisites:
You must have completed Chem 1A and 1B or an equivalent to take this class. Students who attempt to take organic chemistry before Chem 1B, or even concurrently with Chem 1B, have a
90% dropout rate!
Course Website
Smartwork.norton.com (free); search for “Moorpark College Chem M07A”
Top Hat response system ($20); go to tophat.com; look for course 045476
Cheating :
Cheating includes faking results and copying other people’s answers during exams, and using unauthorized electronic devices on an exam.
DO NOT USE YOUR PHONE DURING AN EXAM. EVER!
Secret of Success in O-Chem :
Organic chemistry is a lot like a foreign language. Study a little at a time, but study often. Unlike a lot of other classes you have taken, cramming before an exam will not work after the first few exams! If you find yourself falling behind, get help from a tutor or me. If you don’t become familiar with the basics of the subject, you will fail the next semester. Don’t let it wait!
Try and form small study groups so that you can ask questions of your fellow students.
Access Statement
Students with disabilities, whether physical, learning, or psychological, who believe that they may need accommodations in this class, are encouraged to contact ACCESS as soon as possible to ensure that such accommodations are implemented in a timely fashion. Authorization, based on verification of disability, is required before any accommodation can be made.
The phone number for ACCESS is 378-1461 and they are located on the ground floor of the LMC Building.
Complaints?
Chemistry Dept Chair – Robert Keil
Dean of Physical Sciences – Julius Sokenu; jsokenu@vcccd.edu
; AC 232, 8AM -5PM M–Tr, 8AM - Noon Fri.

Student   Learning   Outcomes:     Chem   7A   At   the   conclusion   of   the   course,   students   will   be   able   to…
1   describe   how   various   organic   molecules   are   used   in   medicine,   industry,   and   the   household   and   how   their   use   impacts   daily   life   and   draw   correct   Lewis   structures   for   a   wide   variety   of   main ‐ group   compounds,   identify   hybrid   and   molecular   orbitals   utilized   in   bonding,   and   convert   formulas   into   various   three   dimensional   structural   representations   including   skeletal   (bond ‐ line)   structures   and   resonance   hybrids.
2   name   cyclic   and   acyclic   compounds   containing   alcohols,
halides,   alkenes   and   alkynes   using   the   IUPAC
(International   Union   of   Pure   and   Applied   Chemistry)   system,   name   small   compounds   using   common   (e.g.,   iso,   sec ‐ ,   tert ‐ )   prefixes,   identify   and   name   compounds   containing   common   functional   groups   such   as   halides,   alkenes,   alkynes,   carbonyl   groups,   alcohols,   amines,   aromatic   rings   and   ethers.
3   identify   conformational   isomers,   draw   Newman   projections   and   cyclohexane   chair   forms   that   accurately   portray   axial   and   equatorial   groups,   and   predict   which   Newman   projection   and   chair   form   will   be   most   stable   and   least   stable.
4   identify   stereoisomers,   label   a   stereocenter   using   the   Cahn ‐ Ingold ‐ Prelog   rules,   distinguish   between   and   define   the
terms   enantiomer,   diastereomer,   meso,   chiral   and   achiral,   and   provide   examples   of   chiral   molecules   without   stereocenters.
5   predict   both   the   magnitude   and   direction   of   the   polarity   of   organic   molecules,   identify   intermolecular   forces   between   organic   molecules,   and   understand   how   intermolecular   forces   influence   boiling   point,   solubility,   nucleophilicity,   and   reactivity   of   organic   compounds.
6   predict   the   course   of   any   acid ‐ base
reaction   based   on   pKa   values   and   organic   structures,   rank   common   functional   groups   in   order   of   their   pKa   values,   draw   “electron   arrows”   to   indicate   the   flow   of   electrons   in   Lewis   acid ‐ base   reactions,   and   identify   various   reagents   that   will   quantitatively   deprotonate   an   alcohol   and   an   alkyne.
7   draw   the   mechanism   and   predict   the   products   of   inter ‐  and   intramolecular   nucleophilic   substitution   (SN)   reactions,   including   stereocenter   inversion   during   an   SN2   reaction,   racemization   of   stereochemistry   during   an   SN1   reaction,   and   carbocation   rearrangements.
Students   should   be   able   to   rank   carbocations   in   the   correct   order   of   stability   and   list   various   groups   in   order   of   their   nucleophilicity   and   use   these   skills   to   rank   the   rate   of   similar   SN   reactions   that   vary   in   the   nature   of   the   substrate.
8   use   Zaitsev’s   rule   to   predict   which   alkenes   will   be   most   stable,   label   alkenes   as   E   or   Z   using   the   Cahn ‐ Ingold ‐ Prelog   rules,   predict   whether   a   given   nucleophile   will   give   predominately   elimination   or   substitution   in   a   reaction,   draw   the   mechanisms   of   E2   and   E1   reactions,   and   use   this   information   to   predict   the   major   and   minor   products   of   substitution   and   elimination   reactions   of   electrophiles   bearing   a   leaving   group.
9   draw   the   mechanism   and   predict   the   products   of   addition   reactions   to   alkenes   and   alkynes   including   reactions   that   demonstrate   the   stereochemical   ramifications   of   the   addition   of   halogens   and   hydrohalogens   (in   the   presence   and   absence   of   water),   the   difference   between   acid ‐ catalyzed   hydration   and   hydroboration   as   methods   of   adding   hydroxy   groups,   and   the   consequences   of   tautomerization   to   the   enol   products   formed   during   hydration   of   alkynes.
10   draw   the   mechanism   and   predict   the   products   of   redox   reactions   of   alkenes   and   alkynes,   including   epoxidation,   stereoselective   dihydroxylation,   ozonolysis,   catalytic   hydrogenation,   and   stereoselective   reduction   of   alkynes   to   cis   and   trans   alkenes.
Also,   plan   synthetic   strategies   using   alkynyl   nucleophiles.
11   draw   the   mechanism   and   predict   the   products   of   substitution,   elimination,   and   redox   reactions   of   alcohols,   ethers,   and   epoxides,   including   the   Williamson   ether   synthesis,   dehydration   reactions   catalyzed   by   acids   and   other   reagents,   conversions   of   alcohols   to   alkyl   halides   using   hydrohalogens   and   other   reagents,   tosylate   formation,   oxidations   of   alcohols   to   form   aldehydes,   carboxylic   acids,   and   ketones,   acid ‐ catalyzed   decomposition   of   ethers,   and   the   stereochemical   ramifications   of   epoxide ‐ opening   reactions   in   the   presence   and   absence   of   acid   catalysts.
12   explain   the   use   of   infrared   spectroscopy   and   mass   spectrometry   in   the   determination   of
organic   chemical   structure,   identify   specific   functional   groups   from   IR   spectral   data,   and   use   IR   and   MS   data   to   make   determinations   about   organic   structures.
13   identify   the   causes   and   origins   of   the   nuclear   magnetic   resonance   (NMR)   effect,   correlate   chemical   shifts   in   NMR   spectra   with   structure   and   predict   the   integrations,   positions   and   peak   splitting   of   signals   in   proton   spectroscopy,   and   be   able   to   both   predict   the   NMR   spectra.

Week of
19-
Aug
26-
Aug
Lecture Monday
Introduction to the course; online portions of the course;
Review of Lewis structures
Bond and molecule polarity; Electron arrows; Acid strength;
Lewis Structures; resonance forms; hybridization; bond
Lengths;
Lecture Wednesday
Lewis structures and electron arrows;
2-Sep Labor Day
9-Sep Finish/Review topics Chap 1-3; Intro to nomenclature
16-
Sep
Alkane nomenclature; Newman Projections; Chair forms
23-
Sep
30-
Sep
Chirality; Plane of symmetry; system); meso
R/S designation (CIP
Finish/Review topics Chap 4-5; Intro to thermodynamics and kinetics
7-Oct Review  H,  G,  S; Energy diagrams;
Functional groups; intermolecular forces; Keq and pKa; Predict acid-base reactions;
Exam One (Chapters 1-3)
Stability of chair forms and Newman forms; Definition of oxidation
Relationships between compounds; enantiomers and diastereomers
Exam Two (Chapters 1-5)
11-
Nov
18-
Nov
25-
Nov
14-Oct
21-Oct
The S
N
2 reaction; leaving group; nucleophile, solvent, R group; examples
The E2 reaction; Base strength; regiochemistry of E2; mechanism and electron arrows
28-Oct Finish/Review topics Chap 6-8
4-Nov
Nomenclature of alcohols and ethers; Synthesis of ROH and ROR; Dehydration reactions; Carbocation rearrangements
Veteran's Day
Addition of X synthesis
2
; hydroboration; halohydrins; organic
Finish/Review topics Chap 9-11
2-Dec
9-Dec
Review oxidation numbers; Hydrogenation; Partial hydrogenation; Epoxidation; Osmylation
Lewis structures and properties of radicals; halogenation of alkanes;
Final: Weds, 12/18 8-10am
Rate laws; catalysts; Nomenclature of Alkyl Halides; Physical properties of Alkyl Halides
The S
N1
reaction; stereochemical differences; leaving group; nucleophile, solvent, R group; deciding on a pathway
The E1 reaction; solvent effects; Electron arrow mechanisms;
Which reaction is it?; Organic synthesis
Exam Three (Chapters 1-8)
POCl
3
; PBr
3
, TsCl; Epoxides; Opening epoxides in acid and base
Nomenclature of alkenes; E/Z notation; Synthesis of alkenes; addition of HX; regiochemistry of addition
Alkyne nomenclature; synthesis of alkynes; application of previous methods to alkynes; acetylide reactions
Exam Four (Chapters 1-11)
Ozonolysis; Partial vs complete oxidation of alcohols; LiAlH
4 and NaBH
4
Allylic halogenation; Polymers

9-Sep
16-Sep
23-Sep
30-Sep
7-Oct
14-Oct
21-Oct
28-Oct
4-Nov
11-Nov
18-Nov
25-Nov
2-Dec
9-Dec
Week of
19-Aug
26-Aug
2-Sep
Lab Monday
Check In - Worksheet
Physical Properties of Compounds: Melting Points
Lab Wednesday
Check In- Worksheet
Review
Labor Day
Recrystallization of Benzoic Acid
Acid-Base Extraction of Benzophenone and Benzoic
Acid
Stereochemistry Model-Building Lab
Review for final
Physical Properties of Compounds: Melting
Points
Recrystallization of Benzoic Acid
Acid-Base Extraction of Benzophenone and
Benzoic Acid
Stereochemistry Model-Building Lab
Infrared Spectroscopy Infrared Spectroscopy
Synthesis of 2-Ethoxynaphthalene:
An SN2 Reaction and Lab Notebook Exercise
Synthesis of 2-Ethoxynaphthalene:
An SN2 Reaction and Lab Notebook Exercise
Gas Chromatography Gas Chromatography
Simple and Fractional Distillation
The Blue Bottle Reaction Mechanism
TLC and column chromatography of a spearmint oil mix
Veteran's Day
A Grignard-like Organic Reaction in Water
GCMS day - Finish Grignard lab
Check Out
Simple and Fractional Distillation
The Blue Bottle Reaction Mechanism
TLC and column chromatography of a spearmint oil mix
A Grignard-like Organic Reaction in Water
Review
GCMS day - Finish Grignard lab
Check Out
Review for final