CHEM 2542 - Organic Chemistry II – Spring 2018

Tentative Lecture Outline - Recommended Reading and Problems - updated 1/10/18

 

This page will be updated by 2 pm on each day of lecture.

  

All chapter numbers and problems refer to the textbook and its solution manual.


Topic covered:

01/10/18:                   Review of material from Organic Chemistry I: electron configuration/electronegativity, polarity of bonds, formal charges, resonance, functional groups.

Recommended Reading: Chapter 1: Sections 1.1,1.2,1.3,1.6; recommended Problems: Textbook 1.1, 1.2, 1.3,1.6,1.9,1.11,1.17-1.20.  Additional Problems Section in Solution Manual:1.26,

01/12/18:                   Review of material from Organic Chemistry I: Aspects of acid/base chemistry . Please review Chapter 2 in the textbook. Recommended problems: 2.1, 2.2, 2.3, 2.4, 2.8.

01/17/18:                   Spectroscopy of Organic Compounds (Chapter 9): Handout_011718.pdf            

9.1. Infrared Spectroscopy.

                                    9.2. NMR Spectroscopy.

                                    9.2.1.Overview of the underlying concepts of NMR spectroscopy.

01/19/18:                   First 5 Minutes: Hydroboration of terminal alkenes (Chapter 6.4); Oxidation of primary alcohols with Chromic acid (Chapter 8.7); Reduction of internal alkynes with H2/Lindlar catalyst (Chapter 7.4);  Dihydroxylation of alkenes (Chapter 6.5.1). Discussion of Chapter 9: Number of signals in the 13C NMR (9.2.2 A); Recommended Problems: 9.1

01/23/18:                   First 5 Minutes: E2-Elimination (Chapter 5.4, recommended problem 5.10); Cyclohexane conformations/cis-trans isomerism (Chapter 3.5, recommended problems 3.14, 3.15); Newman projection (Chapter 3.3, recommended problem: 3.4.).

Chapter 9.2.2.A continued: Number of signals in the 1H NMR. Recommended problems: 9.2 (skip integration), 9.3 (can be answered by solely looking at the number of signals), 9.12 (a and b)

01/23/18:                   Quiz 1 CHEM 2542 Spring 2018 (25 pts)

Quiz format – The majority of the quiz will be in multiple choice format with some additional write-in. The primary focus of this quiz is IR spectroscopy and aspects of NMR spectroscopy (limited to number of signals in 1H and 13C NMR), which will be combined with material from earlier chapters mentioned above. Material reviewed on 01/10/18 may appear as standalone questions on the quiz. For the functional groups problem 1.11 in the textbook will used as template. You are expected to be able to identify all functional groups in problem 1.11.

01/26/18:                   Integration (9.2.2 B), Signal Splitting (9.2.2.C), Chemical Shifts (9.2.2. D). – Recommended Problems: 9.2, 9.3, 9.4, 9.6. 9.7.

 

01/29/18:                   Discussion of spectroscopy problems. Problem A. Problem B.. – Degree of unsaturation/Index of hydrogen deficiency: Recommended Problems: 6.16 and 6.17. Chapter 9: Recommended Problems: 9.5, 9.11c, 9.11e.

 

01/31/18:                   Chapter 9.3 – Mass Spectroscopy.  Examples

                                    Recommended Problems: 9.8, 9.9, 9.10, 9.11.a, b.

Quiz 2 CHEM 2542 Spring 2018 (25 pts)

Quiz format – The majority of the quiz will be in multiple choice format. The quiz may also include some write-in.  The ratio of multiple-choice questions and write-in questions will not be determined until the printing of the quiz, which will occur on 01/31/18 just before class.

The primary focus of this quiz is IR spectroscopy and aspects of NMR spectroscopy .(Number of signals in 1H and 13C NMR, Integration, Signal Splitting and Chemical Shift.), which will be combined with material from earlier chapters mentioned above. There will an overlap concerning material from quiz 1. Any material reviewed from Organic I is fair game. Material reviewed may appear as standalone questions on the quiz.

 

02/02/18:                   Chapter 10:  Organometallic Compounds and Transition Metal Catalysis

Chapter 10.1. Organolithium and Organomagnesium compounds. Chapter 10.2. Compounds of Transition Metals. 10.2.1. Organocopper compounds. Recommended problems: 10.1, 10.2. Based on the class discussion today, you are expected to be familiar with the meaning of oxidation and reduction as applied to organic chemistry: Chapter 6.5 – page 122; recommended problem: 6.11.

02/05/18:                   10.2.2. Palladium-catalyzed coupling reactions.  Recommended problems: 10.3. - Review Oxidation and Reduction, s-character as determining factor of aciditiy/basicity.

 

02/07/18:                   Exam 1 CHEM 2542 Spring 2018 (100 pts)

Exam format – The majority of the exam will be in multiple choice format. The exam will  also include some write-in  - functional groups – similar to question 10 on quiz 1, problem 1.11. in the textbook will be used as template and a spectroscopy problem similar to question 12 on quiz 2  The ratio of multiple-choice questions and write-in questions will not be determined until the printing of the quiz, which will occur on 01/31/18 just before class.

The primary focus of this exam is the whole of chapter 9, and chapter 10 section 10.1, 10.2.1, and 10.2.2, which will be combined with material from earlier chapters mentioned on this webpage. There will an overlap concerning material from quiz 1. Any material reviewed from Organic I mentioned on this page is fair game. Material reviewed may appear as standalone questions on the quiz.

02/09/18:                   First-5-MInutes-Problem. Review aspects of stereochemistry: R/S, enantiomers, diastereomers, meso (Chapter 4). Halogenation of alkenes (Chapter 6.3). Reduction of alkynes (Chapter 7.4).

Chapter 10.2.3: Carbene intermediates and the Simmons-Smith Reaction. Chapter 10.2.4: Alkene metathesis.  Recommended Problems: 10.5, 10.6.

Chapter 11.1: Nomenclature of aldehydes and ketones. Based on the discussion you are expected to be familiar with the structures of the following: formaldehyde, acetaldehyde, acetone, and benzaldehyde. Problem: 11.1

02/12/18:                   First-5-MInutes-Problem.  => epoxides undergo ring opening reactions treated with nucleophiles. The reaction of ethylenoxide with a organolithium or organo magnesium compound followed by hydrolysis results in a primary alcohol.

Chapter 11.2 – General characteristics of aldehydes and ketones; 11.3 Reactions of aldehydes and ketones with carbon nucleophiles; review exam 1 – the key will be send to you just before class. Recommended Problems: 11.2, 11.3, 11.4, 11.5.

02/14/18:                   First-5-MInutes-Problem.

Chapter 11.4. – Reaction with hydride anion. 11.5 – Wittig reaction. 11.6. Reaction with nitrogen nucleophiles (New functional groups: imine, hydrazone, and oxime. Recommended problems:  11.6, 11.7, 11.8, 11.9.

 

 

02/16/18:                   First-5-MInutes-Problem.

                                    11.6. Reaction with nitrogen nucleophiles – Mechanistics aspects, Wolff-Kishner-Reduction. Recommended Problem: 11.11.

 

02/19/18:                   First-5-MInutes-Problem.

11.7. Reaction with water and alcohols. New functional groups: Hydrate, Semi- or Half acetal, Acetal. Recommended Problems: 11.12, 11.13,11.14, 11.15.

 

02/21/18:                   First-5-MInutes-Problem.

                                    11.8. Oxidation of Carbonyl compounds, Recommended problems: 11.16.

                                    Quiz 3: CHEM 2542 Spring 2018 (25 pts)

Quiz format – The majority of the quiz will be in multiple choice format. The exam will also include some write-in  - functional groups. The ratio of multiple-choice questions and write-in questions will not be determined until the printing of the quiz, which will occur on 02/21/18 just before class.

The primary focus of this quiz is the whole of chapter 11 (Sections 11.1-11.7), which spectroscopy will used to combine this material with material from earlier chapters mentioned on this webpage. There will an overlap concerning material from quiz  1 and 2. Any material reviewed from Organic I mentioned on this page is fair game. Material reviewed during the discussion of the First_Minutes_Problems may also appear on the quiz.

 

02/23/18:                   11.9. Enols and Enolate Anions. 11.10. Aldol Reaction. Recommended problems: 11.17, 11.18, 11.19, 11.20, 11.21, 11.22, 11.23, 11.24.

 

02/26/18:                   First-5-MInutes-Problem.

Mixed-Aldol reaction. Introduction Chapter 12 – Carboxylic acid derivatives react via acyl substitution. -  Example – Fischer Esterfication – reaction of carboxylic acid with an alcohol under acidic conditions. Recommended problems:12.9, 12.10.

 

02/28/18:                   Chapter 12. 12.1: Nomenclature – Functional groups discussed: Acid chloride, acid anhydride, ester, amide. Important acid and derivatives: formic acid, acetic acid, benzoic acid, oxalic acid, acetyl chloride, benzoyl chloride,acetic anhydride, ethyl acetate, DMF. 12.2. Physical properties: acidity, boiling points. 12.3. Nucleophilic acyl substitution: Mechanistic aspects, relative reactivity. Recommended problems: 12.1 (a-g), 12.2, 12.3, 12.4, 12.5, 12.6, 12.7.

02/03/18:                   Chapter 12.4: Preparation and interconversion of acid derivatives. 12.4.1 Acid chlorides, 12.4.2. Anhydrides, 12.4.3. Esters. Recommended problems: 12.8, 12.11.

 

03/12/18:                   First-5-MInutes-Problem.

                                    Chapter 12.4. Preparation and interconversion of acid derivatives. 12.4.4. Amides. Reaction with hydride ion.  – Recommended problems: 12.12, 12.13, 12.15, 12.16, 12.17.

 

03/14/18:                   Quiz 4: CHEM 2542 Spring 2018 (25 pts)

Quiz format – The majority of the quiz will be in multiple choice format. The quiz will also include some write-in. The ratio of multiple-choice questions and write-in questions will not be determined until the printing of the quiz, which will occur on 03/14/18 just before class.

The primary focus of this quiz is chapter/section 11.8, 11.9, 11.10, 12. 1, 12.2, 12.3, 12.4, and 12.5, spectroscopy will used to combine this material with material from earlier chapters mentioned on this webpage. Any material reviewed from Organic I mentioned on this page is fair game. Material reviewed during the discussion of the First_Minutes_Problems may also appear on the quiz.  You are expected to be able to recognize all functional groups mentioned on this webpage.

03/16/18:                   12.6: Reaction with Hydride ion continued. 12.7: Reaction with carbanions. Recommended Problems: 12.18, 12.19, 12.20, 12.21.

 

03/19/18:                   First-5-MInutes-Problem.

12.7. Reactions of Enolate anions derived from esters. – Example: enolate of ethyl acetate, claisen condensation of ethyl acetate. Recommended Problem: 12.22.

03/21/18:                   Exam 2: CHEM 2542 2018 (100 pts)

Exam format – The majority of the exam will be in multiple choice format. The exam will also include some write-in. The ratio of multiple-choice questions and write-in questions will not be determined until the printing of the exam, which will occur on 03/21/18 just before start of the exam.

The primary focus of this exam will be whole of chapter 11 and most of chapter 12 (all content from sections 12.1 to section 12.6, material from section 12.7 is limited to content of figure 12.20). Spectroscopy will used to combine this material with material from earlier chapters mentioned on this webpage. You are expected to be able to recognize all functional groups discussed.

03/23/18:                   12.7 Reactions od Enolate anions derived from esters - continued.  Recommended Problems: 12.23, 12.24.

03/26/18:                   Chapter 13: Sections 13.1 - 13.3: Conjugated compounds examples. Highly conjugated compounds absorb visible light and are therefore colored. Conjugate electrophilic addition. 1,2 vs. 1,4-addition; kinetic vs. thermodynamic product.  Conjugate nucleophilic addition. Recommended problems: 13.1.13.2, 13.3, 13.4, 13.5, 13.6.

03/28/18:                   Chapter 13.4.  Recommended Problems: 13.7 and 13.8. Chapter 14.1.

 

03/30/18:                   First-5-MInutes-Problem. Chapter 14.1. Examples of aromatic compounds. Nomenclature -  Chapter 14.2. – You expected to know the structures and names of the following: benzoic acid, benzaldehyde, acetophenone, phenol, aniline and toluene. Recommended problems: 14.1-14.3.

 

04/02/18:                   First-5-MInutes-Problem. – You are expected to review the conversion of alkenes to the diols, epoxides, dihalides and cyclopropanes

 

04/04/18:                   Quiz 5: CHEM 2542 Spring 2018 (25 pts)

Quiz format – The majority of the quiz will be in multiple choice format. The quiz will also include some write-in. The ratio of multiple-choice questions and write-in questions will not be determined until the printing of the quiz, which will occur on 04/05/18 just before class.

The primary focus of this quiz is chapter/section 12.7, chapter 13 and chapter 14.1 and 14.2, Spectroscopy will used to combine this material with material from earlier chapters mentioned on this webpage. Any material reviewed from Organic I mentioned on this page is fair game. Material reviewed during the discussion of the First_Minutes_Problems may also appear on the quiz.

 

04/06/18:                   First-5-MInutes-Problem. – Chapter 14.3 – Electrophilic aromatic substitution.  Recommended Problems: 4.3,4.4,4.6,4.7;14.5-14.7.

 

04/09/18:                   Chapter 14.3 continued. Chapter 14.4

 

04/11/18:                   Quiz 5 – Primary focus - Chapter 14.2, 14.3 and 14.4.

 

Summary of the material discussed for chapter 14.4 as discussed so far:

 

Meta directing: Carbonyl, Nitrile, Sulfur (VI), Nitro, Ammonium

 

Ortho/Para directing:  OR  (R=H, Alkyl, ester), amine, amide, phosphorus(III), sulfur (II), halogens (Cl, Br, I).

           

As for chapter 14.2 you are expected to be able to know the structure of the following: benzoic acid, benzaldehyde, acetophenone, phenol, aniline, toluene.

 

Recommended problems: 14.5, 14.6, 14.7, 14.8 (skip bromination of toluene), 14.9 c, 14.11.

                                               

From earlier chapters based on the class discussion on 04/06/18 and 04/09/18:

 

Newman projection, Fischer projection, R/S

Carbocationic rearrangements

Wolf-Kishner reduction

Fischer Esterfication and synthesis of ester from carboxylic acids via preparation of the acid chloride, followed by treatment of acid chloride with an alcohol  Preparation of Grignard reagents

Preparation of carboxylic acids from Grignard reagents by treatment of CO2 followed by acidic hydrolysis.

 

You can expect spectroscopy on the quiz.

 

 

04/13/18:                   First-5-MInutes-Problem. – Chapter 14.4. Chapter 14.5.1.  Recommended Problems: 14.8,14.9, 14.11, 14.13.

 

 

 

04/16/18:                   First-5-MInutes-Problem.

Chapter 14.5.2, Chapter 14.6, 14.7. Recommended problems: 14.12, 14.14, 14.15, 14.16, 14.17.

 

04/18/18:                   Exam 3

 

Primary focus – Chapter 12.7, Chapter 13 and Chapter 14.

 

As discussed on 4/13/18 class, exam 3 may include any of the following (I will use Dr. Zhdankin’s exams from Fall 2017 as template for questions concerning this material. http://www.d.umn.edu/%7Evzhdanki/2541/exams/)

 

Newman projections – staggered/eclipsed/gauche.

Fischer projection.

Dash/wedge type structures.

R/S configuration

meso compound

enantiomers/diastereomers

 

Exam 3 will also contain spectroscopy.

 

 

04/2018:                    Chapter 15.1-15.2: First-5-MInutes-Problem.  Recommended problems: 15.1, 15.2,.15.3,15.4,15.5.

 

04/23/18:                   First-5-MInutes-Problem.  Chapter 15.3.  – New material: Reduction of aromatic nitro compounds to aniline derivatives – Reagent HCl/Fe or Sn. Reductive amination – Formation of a secondary amines by treatment of a aldehyde or ketone with a primary amine followed by reduction. One step/one pot variant: Ketone/Aldehyde + primary amine + NaBH3CN; Two step variant: Step 1: Convert ketone or aldehyde to imine. Step 2: reduce amine with NaBH4. – You are expected to review of SN2 and SN1; mechanisms, substrate, stereochemistry and kinetics. – Recommended problems: Please review elimination reactions.

 

 

04/25/18:                   First-5-MInutes-Problem.  Chapter 15.4 and 15.5.1. – Recommended problems: 15.9 b, 15.10 a,.

 

04/27/18:                   First-5-MInutes-Problem. 

 

 

 

 

 

 

 

 

 

                                   

                                   

 

 

 

 

 

 

 

 

 

 

 

 

 

                                                                                   

                                                 

 

 

 

 

 

                                   

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

General Lecture Outline:

“Organic Chemistry: a Two-Semester Course of Essential Organic Chemistry” by Zhdankin and Grundt:

Chapter 9. Spectroscopy of Organic Compounds

Chapter 10. Organometallic Compounds and Transition Metal Catalysis

Chapter 11. Aldehydes and Ketones

Chapter 12. Carboxylic Acids and their Derivatives

Chapter 13. Non-cyclic Conjugated Systems

Chapter 14. Benzene and Aromatic Compounds

Chapter 15. Amines

Chapter 16. Introduction to Bio-molecules