UCD Chem 128B: Franz

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Chapter Order, Topic Coverage, and Suggested Practice Problems

This course is designed for Chemistry and Engineering Majors. Chapters 10-14 and 16-19 in the lecture text plus parts of Chapter 15 must be completed (see below for more details). It is strongly suggested that you establish a work schedule that allows you to READ AHEAD in the textbook. Even though you may not understand the material fully at first, your familiarity with the ideas will help you get much more out of the lectures and your subsequent studying. Students should also read the “Chemical Connections” sections for interest and relevance. This material is fair game for all quizzes (especially potential extra credit questions).

Suggested Practice Problems. These problems assignments are from the chapters in your textbook and are given as a guide for studying and for self-testing your mastery of the material covered in lectures – they should be worked on after the material is presented in lecture. Answers for these problems are given in the “Study Guide and Solution Manual.” Each quiz will have one or more questions that are taken directly from one of the suggested problems in the textbook.

Course Overview; Properties of alcohols, hydrogen bonding 10.1-10.4
Reactions of Alcohols 10.5-10.7
Reactions of Alcohols con!t, Oxidation Reactions 10.5-10.8
Protecting Groups, Properties of ethers, Synthesis of ethers 11.6, 11.1-11.4
Synthesis and Reactions of Epoxides 11.7-11.10
Organometallic compounds, reactions with epoxides 15.1-15.2
Synthesis Strategies and Practice
Structure and Properties of Aldehydes and Ketones;
Aldehydes and Ketones as electrophiles 16.1-16.4
Addition of Carbon Nucleophiles to Aldehydes and Ketones 16.5A-C, 16.11A
Introduction to Spectroscopy; IR Spectroscopy 12.1-12.5
Proton and Carbon NMR Spectroscopy 13.1-13.7, 13.11
More NMR Spectroscopy and Practice Problems 13.8-13.10, 13.12
Mass Spectrometry; Practice Problems 14.1-14.4
Back to Carbonyls… Wittig reaction; Synthesis 16.6
Addition of Oxygen and Nitrogen Nucleophiles 16.7-16.8
Oxidations of Aldehydes, Reductive Amination 16.10, 16.11D
Acidity of !-hydrogens, Keto-enol tautomerization;
Introduction to reactions of enolates 16.9, 16.12
Properties, Synthesis and Reactions of Carboxylic acids 17.1-17.5
More Reactions of Carboxylic acids 17.6-17.9
Properties and Reactions of Carboxylic acid derivatives 18.1-18.4
More Reactions of Carboxylic acid derivatives 18.5-18.10
Aldol and Claisen Condensation Reactions; Synthesis 19.1-19.4
Other Eeactions of Enolates and Enamies; Synthesis 19.5-19.8
Synthesis Strategy Overview and Final Review

CHAPTER 10, Alcohols:

2, 4-12, 14-16, 18-23, 25-28, 29-32, 34, 35, 37-41, 43, 45, 47, 49, 51-52, 55, 57-59

CHAPTER 11, Ethers & Epoxides: (skip sections 11.11-12)

2-4, 7, 10-13, 15-16, 19-21, 23, 25, 27, 29, 31, 33-36, 38, 40, 44, 47

CHAPTER 15, Organometallic Compounds: (only sections 15.1 and 15.2)

1, 2, 7ab, 11, 12a, 20d, 21, 23

CHAPTER 16, Aldehydes & Ketones: (only sections 16.1 – 16.5C and 16.11A)

(Chapter 15) 17, 18

(Chapter 16) 4, 12, 14, 15, 18-22, 51, 52abd, 54, 55, 59, 62bc, 68, 73a, 78

CHAPTER 12, Infrared Spectroscopy: 1-9, 11

CHAPTER 13, Nuclear Magnetic Resonance Spectroscopy:

2-9, 12, 13, 15-18, 20, 22, 23, 24a-j; also 16 and 17 from Chapter 16

CHAPTER 14, Mass Spectrometry: 4-9, 14, 16, 24a, 25a

CHAPTER 16, Aldehydes & Ketones: (remaining sections)

5-11, 14-17, 23-25, 27, 29-34, 38-41, 43-46, 60, 73d, 80

CHAPTER 17, Carboxylic Acids:

1, 2, 4-10, 15-17, 18d, 19-21, 22abd, 23, 25-30, 32, 33, 35-40, 43, 44, 46, 48, 51-53

CHAPTER 18, Functional Derivatives of Carboxylic Acids:

1-17, 19-23, 25-28, 30-33, 35, 39, 41-44, 52, 53, 56, 57-59

CHAPTER 19, Enolate Anions & Enamines: (skip section 19.9)

1-7, 9, 10, 12, 14, 18-22, 24, 26, 27, 29-35, 39, 40, 45-47, 50, 58, 61, 65

** Working these problems where there are several examples of the same concept with different molecules is one of the most important methods to identify patterns, learn strategies and build skills.