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Master Course Outline
CHEM& 262
Organic Chemistry w/Lab II
Course Description: This course is a continuation of CHEM& 261. Structure, nomenclature, reactions
and synthesis of aldehydes, ketones, and aromatic compounds. Grignard synthesis of alcohols. Free
radical reactions.
Credits: 6
Prerequisites: A grade of “C-“or better in CHEM& 261, or instructor permission
Recommended Preparation: none
Co-requisites: none
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Functional group transformation by nucleophilic substitution
Relative reactivity of halide leaving groups
The SN1 and SN2 mechanisms of nucleaophilic susbstitution
Nuclephiles, nucleophilicity, and steric effects
Carbocation stability, rearrangements, and stereochemistry of SN1 reactions
Effect of solvent on the rate of nucleophilic substitution
Substitution and elimination as competing reaction s.
Nucleophilic substitution and elimination of alkyl sulfonates
Sources of alkynes
Nomenclature and physical properties of alkynes
Structure and bonding in alkynes
Acidity of acetylene and terminal alkynes
Preparation of alkynes by elimination reactions
Reactions of alkynes: hydrogenation, metal-ammonia reduction, addition of hydrogen halides,
hydration, addition of halogens, and ozonolysis
Conversion of enols to ketones
Conjugation in alkadienes and allylic systems
The allyl group, and allylic carbocations
SN1 and SN2 reactions of allylic haides
Allylic free radicals and anions
Allylic halogenations
Classes of dienes and relative stabilities of dienes
Bonding in conjugated dienes and in allenes
Preparation of dienes
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Reactions of dienes: addition of hydrogen halides to conjugated dienes, halogen addition to
dienes, Diels-Alder reaction
molecular orbital analysis of the Diels-Alder reaction
The structure and stability of benzene
Orbital hybridization and molecular orbitals of benzene
Substituted derivatives of benzene and their nomenclature
PAH’s
Physical properties of arenes
Reactions of arenes: Birch reduction, free-radical halogenations of alkylbenzenes, oxidation of
alkylbenzenes
SN1 and SN2 reactions of benzylic halides
Preparation of alkenylbenzenes
Addition reactions of alkenylbenzenes
Free-radical polymeriztion
Cyclobutadiene and cyclooctatetrene
Hückel’s Rule
Annulkenes
Aromatic ions
Heterocyclic Aromatic Compounds and Hückel’s Rule
Representative Electrophilic Aromatic Substitution reactions of benzene: nitration, sulfonation,
halogenation, bromination, Friedel-Crafts alkylation and acylation
Synthesis of alkylbenzenes by acylation-reduction
Rate and Regioselectivity of in Electrophilic Aromatic Substitution
Substituent effects in Electrophilic Aromatic Substitution
Multiple substituent effects in Electrophilic Aromatic Substitution
Substitution in heterocyclic aromatic compounds
Nucleophilic aromatic substitution
The addition-elimination mechanism of nucleophilic aromatic substitution
Related nucleophilic aromatic substitution
Introduction to IR pectroscopy
Characteristic absorption frequencies
UV-VIS spectroscopy
Mass spectroscopy
Molecular formula as a clue to structure
Organometallic nomenclature
Carbon-metal bonds in organometallic compounds
Preparation of organolithium and organomagnesum compounds: Grignard reagents
Organolithium and organomagnesum compounds as Brønsted bases
Synthesis of alcohols using Grignard reagents, and organolithium reagents
Retrosynthetic analysis
Alkane synthesis using organocopper reagents
Lithium dialkylcuprates
Transition metal organometallic compounds
Sources of alcohols
Preparation of alcohols by: reduction of aldehydes and ketones, reduction of carboxylic acids,
epoxides
Preparation of diols
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Reactions of alcohols: conversion to ethers, esterification, xidation, including biological and
DMSO oxidation
Oxidative cleavage of vicinal diols
Nomenclature of ethers, and epoxides
Structure and bonding in ethers and epoxides
Physical properties of ethers
Preparation of ethers: Williamson Ether synthesis
Acid catalyzed cleavage of ethers
Preparation of epoxides by conversion of vicinal halohydrins
Reactions of epoxieds: nucleophilic ring opening, acid-catalyzed ring opening
Epoxides in biological processes
Course Resources/Textbooks/Website:
These textbooks are required for this course as well as the beginning course of the sequence, CHEM 261,
and are used for the remaining course in this sequence, CHEM 263
Organic Chemistry, 8th Edition, Frances Carey and Robert Guiliano, McGraw Hill,
ISBN: 987-0-07-340261-1
Organic Chemistry Laboratory Manual, , 3rd Edition, Anne Padías, Hayden McNeil,
ISBN: 978-0-7380-3748-6
Making the Connection2, A How-To Guide for Organic Chemistry Lab Techniques, Anne Padías,
Hayden McNeil, ISBN: 978-1-4292-8812-5
Students are also required to purchase an Organic Chemistry Laboratory Notebook, Hayden
McNeil, ISBN: 978-1-930882-46-1
Other ancillary materials are available from the publisher such as Student Solution Manuals
which, is recommended but is optional. If you have questions about the text, please contact
Julie Nelson at jnelson@ghc.edu.
These items are all available at the GHC Bookstore.
Academic Integrity: All forms of cheating, falsification, and plagiarism are against the rules of this course
and of Grays Harbor College. Students who are unsure what constitutes academic dishonesty are
responsible for asking the instructor for clarification. Instances of intentional academic dishonesty will
be dealt with severely.
Disabilities: Students who have documented disabilities that require accommodations in compliance
with the Americans with Disabilities Act should contact the Disability Support Services coordinator as
well as the instructor of the course in order to ensure that together we create an optimal environment
for educational achievement.
W Day, the final day to officially withdraw from a course, is the Thursday of the seventh week (Thursday
of the fourth week for summer quarter). Students who do not withdraw by that date will receive the
grades they have earned, regardless of whether they are attending the course or completing the work.
Students who are considering withdrawal are strongly advised to consult with the instructor, advisor and
financial aid prior to withdrawing. The only withdrawals allowed after W Day are complete withdrawals
from all courses.
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