Chemistry 250: Reactivity 1 Spring 2013 Tentative Even Day Class Schedule Resources • Workbook: Principles of Reactivity 1 Available in the CSB Bookstore • Text: Choose one or more of the following options: 1. Chemistry 250 Custom Book -- shrink-wrapped with 2 passcodes (strongly recommended) Note answers are available for organic in-chapter problems and biochem end of chapter problems within your text Note answers for the inorganic chapters and some organic (end of chapter problems) are available on the NMR Moodle page 2. Online Text (Structure & Reactivity, Part III, available at: ( http://employees.csbsju.edu/cschaller/ROBI1.htm ) OR if desired a softcover copy of online textbook: (http://academicpub.sharedbook.com/serve/ac/acapub/student_produ ct_page.html?slug=1344449420_58_488) • Online homework passcodes: (ONLY if you didn’t buy text with passcodes) o Two Passcodes: 1) Hornback & 2) Garrett & Grisham: (http://www.cengage.com/owl/) OWL with Cengage 24 months Instant Access Code for Garrett/Grisham's Biochemistry, 5th Ed ISBN-10: 1-133-35236-7 ISBN-13: 978-1-133-35236-5 $113.00 OWL (24 months) Instant Access Code for Organic Chemistry, 1st Edition ISBN-10: 0-495-05102-0 ISBN-13: 978-0-495-05102-2 $74.00 o There may be students from Fall 2012 Chem 251 with extras that will sell at a discount.
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Chemistry 250: Reactivity 1
Spring 2013 Tentative Even Day Class Schedule
Resources • Workbook: Principles of Reactivity 1
Available in the CSB Bookstore
• Text: Choose one or more of the following options: 1. Chemistry 250 Custom Book -- shrink-wrapped with 2 passcodes
(strongly recommended) § Note answers are available for organic in-chapter problems and
biochem end of chapter problems within your text § Note answers for the inorganic chapters and some organic (end of
chapter problems) are available on the NMR Moodle page
2. Online Text (Structure & Reactivity, Part III, available at: ( http://employees.csbsju.edu/cschaller/ROBI1.htm )
OR if desired a softcover copy of online textbook: (http://academicpub.sharedbook.com/serve/ac/acapub/student_product_page.html?slug=1344449420_58_488)
• Online homework passcodes: (ONLY if you didn’t buy text with
passcodes)
o Two Passcodes: 1) Hornback & 2) Garrett & Grisham: (http://www.cengage.com/owl/)
OWL with Cengage 24 months Instant Access Code for Garrett/Grisham's Biochemistry, 5th Ed ISBN-10: 1-133-35236-7 ISBN-13: 978-1-133-35236-5 $113.00 OWL (24 months) Instant Access Code for Organic Chemistry, 1st Edition ISBN-10: 0-495-05102-0 ISBN-13: 978-0-495-05102-2 $74.00
o There may be students from Fall 2012 Chem 251 with extras that will sell
at a discount.
Getting Started on OWL Chemistry 250
There are 2 separate online passcodes you will need to use, so you will need to go through the following procedure twice. On the web, go to: http://owl.cengage.com In the box labeled Instructor/Student Login, click on: Organic Or Biochemistry Go through the books and choose: Organic Chemistry, 2nd Ed; Hornback Or Biochemistry, 5th Ed; Garrett&Grisham Go through the list of schools and choose: College of Saint Benedict - Saint Joseph, Minnesota Select: Student registration Select: Chemistry 250 Spring 2013 with Instructor Name
Make sure you select the correct section! Choose your own loginid and password and enter the access code you bought with your book Two Notes:
These passcodes will be good for all next year (DON”T throw them away!) and you will have to re-register each semester. We will begin using the organic passcode in January and the biochemistry passcode in March – Keep them in a safe place!
Anionic Nucleophilic Additions to Carbonyls Tuesday, January 15, Day 2
Overview • First-Day Overview of Class Structure
o Roster o Syllabus and Course Outline
• Group work and Pedagogical Theory • Assign Groups
In class: Nu Additions
• Introduction to Anionic Nucleophilic Additions to Carbonyls o Mechanism, Workbook: 3-9 o Acetylides, Cyanides and Grignards, Workbook: 10-12
Note Upcoming Deadline:
• OWL Review Packet 1: Due Jan 23 Ch 1: Chemical Bonding Ch 2: Organic Structures and Electrostatics Ch 3: MO Ch 4: Acid-Base Ionic Radii Resonance Structures
• OWL Review Packet 2: Due Feb 12 Ch 7: Stereochemistry Ch 16: Aromaticity
Chapter 5/12: Nomenclature: OWL 5bdghi, 12bd
• MLK Extra Credit: Percy Julian (Due Thursday, Jan 23)
Tuesday, January 15 6:30-8:00 pm Faculty Tutorial, O’Connells
2) After watching the movie, follow at least one related interactive link at the
bottom of the PBS Julian website.
3) Write a response to the movie and website (2-3 pages):
a. Summary of Percy Julian’s scientific achievements
b. Mention of the obstacles that Percy Julian faced
c. Discussion of the link that you followed
d. Brief Conclusion with a personal response regarding something that you
learned
4) Due Tuesday, January 22nd.
Thursday, January 17, Day 4 Preparation: Nu Additions
• Read: o Reactivity 1 text: Chapter 18. Additions to the Carbonyl Group
§ 18.1 General Mechanisms o Structure & Reactivity online text: CO1-CO4, CO6 o Reactivity 1 text: Chapter 18. Additions to the Carbonyl Group
§ 18.2 Addition of Hydride § 18.4 Addition of HCN § 18.5 Preparation and Properties of Organometallic
Nucleophiles § 18.6 Addition of Organometallic Nucleophiles
o Structure & Reactivity online text: CO7-CO8, CO16 • Suggested Practice Problems:
o Reactivity 1: 18.1, 18.2, 18.6, 18.8, 18.9, 18.10 § NOTE: Answers are found in NMR Moodle Site
o Structure and Reactivity: CO1.1-1.3, CO2.1-2.2, CO3.1-3.3, CO4.1, CO6.1-6.2
§ NOTE: Answers are found in CO22 • Homework due:
o Introduction to OWL: How to Complete and Submit Assignments
o OWL: 18a (Tutor, Carbonyl Reactions) o Passport: Practice problems
• Structure and Reactivity: CO1.1, CO5.1, CO8.1
In class: Nu Additions • Anionic Nucleophiles
o Hydrides, Workbook: 13-14 o MO of Nucleophilic Addition, Workbook, 15-16 o Chiral Hydrides, Workbook: 17-18 o Practice, Workbook: 19-22 o Sample Notecards, Workbook: 23
Thermodynamics Monday, January 21, Day 6
Preparation: Thermodynamics of Reactions • Read:
o Reactivity 1 text: § Chapter 6.2 Two Keys to Stability of TM Complexes
o Structure & Reactivity online text: TD1-TD3 • Suggested Practice Problems:
o Structure & Reactivity, Part III: TD 1.1, 2.1, 3.1, 3.2, 3.3 NOTE: Answers are found in TD7
• Homework due: o Group Assignment: Bio Hydrides, Roadmap Practice, Workbook:
19-21 o Passport: Bring Notecards of new reactions, Workbook: 22 o OWL: 18b, 18c, 18d
o Reactivity 1 text: § Chapter 2.3 Modern View of CC compounds § Chapter 2.4 An Introduction to Nomenclature § Chapter 6.2 Two Keys to Stability of TM Complexes
o Structure & Reactivity online text: CC1-CC7 o Organometallic Reader: Simplifying OM Complexes
§ Part I § Part II § Part III
o Organometallic Hypertext: § Denticity § Electron Counting
• Suggested Practice Problems: o Structure & Reactivity, Part III: CC 3.1-3.7, 4.1-4.8, 6.1-6.9 o NOTE: Answers are found in CC11
• Homework due: o Group Homework, Workbook: 84-86 o Individual Homework on Nomenclature: Workbook: 91-92 o OWL: Review Packet 2 Due (Stereochemistry and Organic
o Catalysis and Reaction Energetics • Suggested Practice Problems:
o Structure & Reactivity, Part III: • Homework due:
o Group Homework: Magnetism, 170-174 o OWL: Ligand Exchange, Magnetic Properties, Magnetic
Moments
In class: Catalysis • Catalysis, Workbook: 206-217 • PSA#4
Tuesday, February 19 No Faculty Tutorial
Thursday February 21-24th
LONG WEEKEND
Carbonyl Binding and Migratory Insertion Tuesday, February 26, Day 6
Preparation: Nu Additions • Read:
o Structure & Reactivity online text: MI1, MI2, MI3 o Organometallic Reader:
§ Carbon Monoxide o Organometallic HyperText:
§ Insertion Reactions • Suggested Practice Problems:
o Structure & Reactivity, Part III: TD 6.1, 6.2, 6.3, 6.4, 6.5 § NOTE: Answers are found in TD7
o Structure and Reactivity: CO15.1-15.8 § NOTE: Answers are found in CO23
• Homework due: o Individual Passport, Catalysis Summary: Workbook: 218 o Group Homework: LAD, Workbook: 220-221
In class: Nu Additions
• Carbonyl Binding and Migratory Insertion, Workbook: 226-231 • PSA#5
Tuesday, February 26 6:30-8:00 pm Faculty Tutorial, O’Connells
Thursday, February 28, Day 2 Preparation: Nu Additions
• Read: o Structure & Reactivity online text: MI4, MI5 o Organometallic Insertion Reactions
§ Insertions o Organometallic HyperText:
§ β-hydride Elimination • Suggested Problems:
o Structure & Reactivity, Part III: MI1-MI5 § NOTE: Answers are found in MI6
• Homework due: o Group Homework, Application Problems: Workbook: 232-233
In class: Nu Additions
• 1,2-Insertion and β-elimination, Workbook: 233-238
Nucleophilic Additions to Carbonyls: Part 4 Monday, March 4, Day 4
Preparation: Nu Additions • Read:
o Reactivity 1 text: Chapter 18. Additions to the Carbonyl Group § 18.7 Wittig Reactions
o Structure & Reactivity online text: CO18 • Suggested Problems:
o Structure & Reactivity, Part III: MI1-MI5 § NOTE: Answers are found in MI6
• Homework due: o Passport: Insertions and Eliminations, MI5.1, 5.2, 5.3, 5.4 o Group Homework, Instructor Assigned: Workbook: 237-242 o OWL: 18e (Wittig Tutor), Migratory Insertion
In class: Nu Additions
• Sulfur and Phosporus Ylides, Aldols, Workbook: 248-250 Wednesday, March 6, Day 6
Preparation: Nu Additions • Read:
o Reactivity 1 text: Chapter 20: Enolates and Other Carbon Nucleophiles
§ 20.1 Enols and Enolates § 20.5 Aldol Condensations
o Structure & Reactivity online text: CO9 • Suggested Practice Problems:
o Reactivity 1: Wittigs § Wittigs: 18.12, 18.13, 18.14, 18.15 § NOTE: Answers are found on NMR Moodle site
o Structure and Reactivity: CO18.1-18.6 § NOTE: Answers are found in CO23
• Homework due: o Individual Homework, Enolates: Workbook, 252-255
In class: Nu Additions
• Applications of Ylides/Enolates to Synthesis, Workbook: 251, 256-266
Tuesday, March 5 6:30-8:00 pm Faculty Tutorial, O’Connells
Nucleophilic Substitutions Friday, March 8, Day 2
Preparation: Nu Substitutions • Prepare Notecards on Carbonyl Addition Reactions • Read
o Reactivity 1: Chapter 19. Nucleophilic Additions to Acid Derivatives
§ 19.1 General Mechanism § 19.2 Preparation of Acyl Chlorides § 19.3 Preparation of Anhydrides § 19.4 Preparation of Esters § 19.5 Preparation of Carboxylic Acids
o Structure & Reactivity online text: CX1-CX4 • Suggested Practice Problems:
o Reactivity 1: Wittigs § Aldols: 20.2, 20.9, 20.10 § NOTE: Answers are found on NMR Moodle site
o Structure and Reactivity: CO9.1-9.12 § NOTE: Answers are found in CO23
• Homework due: o Group Homework: Do either of these sets of practice problems
§ Reactivity 1 text: 18.5, 20.9 o Individual Homework, Callystatin, Workbook, 266 o OWL: 20a, 20f, 20g
In class: Nu Substitutions
• Ski Slope, Workbook: 271-272 • March PSA
Tuesday, March 12, Day 4 Preparation: Nu Substitutions
• Read o Reactivity 1: Chapter 19. Nucleophilic Additions to Acid
Derivatives § 19.7 Reaction with Hydride Nucleophiles § 19.8 Reduction of Acid Derivatives to Aldehydes § 19.9 Reaction with Organometallic Reagents § 20.7 Haloform Reactions
o Structure & Reactivity online text: CX5-CX6 • Suggested Practice Problems:
o Reactivity 1: 19.2-19.16 § NOTE: Answers are found on NMR Moodle site
o Structure and Reactivity: CX1.1, CX2.1-2.2, CX3.1-3.3, CX4.1-4.5 § NOTE: Answers are found in CX9
• Homework due: o Passport Homework: Workbook, 273 as notecards o OWL: 19a, 19b (Tutors)
In class: Nu Substitutions
• Substitutions, Workbook: 274-279 **Register for OWL, Garrett and Grisham, 5th Ed. Biochemistry Review Packet due March 21
(BIG assignment, LOTS of points – PLAN Ahead)
Tuesday, March 12 6:30-8:00 pm Faculty Tutorial, O’Connells
Thursday, March 14, Day 6 Preparation: Nu Substitutions
• Read: o Reactivity 1: Chapter 19. Nucleophilic Substitutions to Acid
Derivatives § 20.6 Ester Condensations § 19.11 Derivatives of Sulfur and Phosphorus Acids
o Structure & Reactivity online text: CX7-CX8 • Suggested Practice Problems:
o Prepare Notecards on Carbonyl Substitution Reactions o Reactivity 1: 19.17-19.24
§ NOTE: Answers are found on NMR Moodle site o Structure and Reactivity: CX5.1-5.7, CX6.1-6.10
§ NOTE: Answers are found in CX9 • Homework due:
o Group Homework: Workbook, Weinreb Amides, 295-296 o OWL: 19c, 19d, 19e, 19f, 19g o OWL: 20h (Tutor)