Reading for Friday

Sections 15.6-15.10

Chem 626 Organic Chemistry 2

Spring 2013
Prerequisite: Chem 624 or equivalent

Instructor: Prof. David R. Benson

5070 Malott Hall Office Hours Mon. and Wed. 11 AM-Noon Thurs. 10-11 AM or by appointment

Head TA: Jessica Lohrman

5017 Malott Hall Office Hours Tues. 11 AM Noon Thurs. 2-3 PM or by appointment

Course Email Address:

chem626@ku.edu
Please use this account for all course-related questions

Required Course Materials:

1) Janice Gorzynski Smith: Organic Chemistry (3rd Ed.) McGraw-Hill, 2011
Special KU Edition

Required Course Materials:

Four (4) Copies of the textbook are on reserve in Anschutz Science Library 2) Connect Plus Electronic Homework System: Packaged with the special KU version of the textbook (sold only in the KU bookstore and other local textbook outlets). May be purchased separately online (see Blackboard for info)

If you set up a Connect account for CHEM 624 last semester, it will still be active for this semester. Registration instructions for new users are available on Blackboard

Recommended materials
1) Student Study Guide and Solutions Manual for the textbook (ISBN: 978-0-07-304987-8) 20 copies of this manual are on reserve in Anschutz Science Library

Recommended materials
2) Molecular Models Available in the bookstores; Other types available online (Molecular Models tab on Bb has my recommendation) A set is also on reserve in Anschutz Science Library

How you can get help outside of class

1) Visit us during office hours 2) Contact us via the course e-mail account 3) Form/join a study group 4) Attend PLUS sessions

CHEM 626 PLUS Sessions SP13

Monday Tuesday Wednesday Thursday Friday Saturday 3:00-4:30 PM 4:00-5:30 PM 3:00-4:30 PM 5:30-7:00 PM 2:30-4:00 PM 10:30-Noon MS 107 MAL 2007 MS 107 MAL 2007 MAL 2007 MAL 2007

Dr. Benson will hold a discussion/review session the Tuesday evening before each exam Time: 6:30 pm Location: 1001 Malott

Sessions begin Monday 1/28

Exam Schedule (6:00-7:30 PM) Exam 1: Thursday, February 21 Exam 2: Thursday, March 14 Exam 3: Thursday, April 11 Exam 4: Thursday, May 2 Final : Wed., May 15, 7:30 AM *All exams in 120 Budig *No Make-up exams!

Inform us of valid EXAM CONFLICTS at least two weeks in advance, so we can arrange an alternate time for you to take the exam Valid time conflicts are activities that you know about in advance and that are integral to your KU academic program (other classes, exams, conference attendance, etc.) or athletic program. *You will be required to provide documentation of the conflict*

Conflicts do NOT include planned or unplanned absences resulting from, for example, illness, family emergencies, or trips out of town for personal reasons The fact that such events are sometimes unavoidable is part of our rationale for using only your top three hour exam scores in determining your grade

Electronic Quizzes: Approximately bi-weekly quizzes (each worth 10 points) will be administered via Connect. The quiz schedule has been posted to Blackboard

Course Grading Top 3 hour exams Top 7 quizzes Final Exam Total:

300 pts 70 pts 200 pts 570 pts

Lecture Materials on Bb
1) Powerpoint slides (pdf format) Course Documents tab 2) Audio recording EchoCenter tab

Classroom Conduct
*Newspapers *Talking *Laptop Computers *Cell phones, texting, etc. *Packing up to go.

Chapter 15 Radical Reactions

Radicals (15.1)
A radical is a reactive intermediate

C-H BDEs (from Table 6.2)

Methyl 1 1

with a single unpaired electron

Relative stabilities of radicals can be

Bond H (kJ/mol) CH3H 435 CH3CH2H 410 410 CH3CH2CH2H (CH3)2CHH 397 2 (CH3)3CH 381 3

predicted from bond dissociation energies (BDEs)

Comparing the 1 and 2 C-H bonds in propane

Radical Reactions (15.2, 15.2A)

Initiators of radical reactions contain

weak bonds that can be broken by heat or light

Examples include halogens (X2) and

peroxides (ROOR)

Bond strength: Radical stability:

1 > 2 2 > 1

Bond Dissociation Energies of some common radical initiators

Bond ClCl BrBr HOOH H (kJ/mol) 242 192 213

Halogenation of Alkanes (15.3)

Radical substitution reaction R-H + X2

h or

R-X + H-X

X2 = Cl2 or Br2

Evidence for Radical Chain Mechanism rather than Ionic Mechanism (15.4)
, h or added peroxide (ROOR) is

Chlorination of Ethane (Fig. 15.4)

necessary for the reaction

O2 inhibits the reaction No rearrangements are observed Unlike carbocations, radicals do not rearrange