Study Page for McMurry 9th Edition

If you are studying a particular chapter in Organic Chemistry, 9th Ed. by John McMurry, the links below cite what lessons in the Primer to read as a study aid for related topics. Then there is a link to a playlist to see explained practice problems for the topics. You can read the Primer before, after, or instead of reading the chapter. You'll have to see what works best for you and assess how much time you have. The Primer reading is WAY shorter than the text book reading if you are in a time crunch and you need to hit some of the high points.

Chapter 1 

Step 1: Quick Reading
From Organic Chemistry 1 Primer 2018

7 pages to read in the Primer

Lessons I.1 (3 p) Representation of Structure

Lesson I.6 (4 p) Hybridization

Step 2: Watch Videos
Explained Problems on Proton Guru Channel

Chapter 2

Step 1: Quick Reading
From Organic Chemistry 1 Primer 2018
Step 2: Watch Videos
Explained Problems on Proton Guru Channel

​17 pages to read in the Primer

Lesson I.2 (5 p) Polarity, Dipoles, Formal Charge

Lesson I.3 (2 p) Intermol. Forces, B.P. and M.P.

Lesson I.7 (4 p) Resonance

Lesson I.9 (2 p) Acids and Bases Definitions

Lesson 1.10 (4 p) Predict Acid/Base Strength

Chapter 3

Step 1: Quick Reading
From Organic Chemistry 1 Primer 2018

11.5 pages to read in the Primer

Lesson I.4.2 (2.5 p) Functional Groups

Lesson I.14 (6 p) Naming Molecules

Lesson I.15 (3 p) Conformers of Ethane/Butane

Step 2: Watch Videos
Explained Problems on Proton Guru Channel
Note:  This chapter covers functional groups but not Nucleophiles/Electrophiles. So, you can skip over the problems about nucleophiles/electrophiles in Video Lesson I.4. Likewise, this chapter only names alkanes, so skip naming alkyl halides and alcohols in video practice I.14.

Chapter 4

Step 1: Quick Reading
From Organic Chemistry 1 Primer 2018

5 pages to read in the Primer

Lesson I.16 (5 p) Cycloalkanes and Chair Cyclohexane

Step 2: Watch Videos
Explained Problems on Proton Guru Channel

Chapter 5

Step 1: Quick Reading
From Organic Chemistry 1 Primer 2018

​9 pages to read in the Primer

Lesson I.17 (2 p) Chirality

Lesson I.18 (4 p) Assigning R- and S-

Lesson I.19 (1 p) Fischer Projections

Lesson I.20 (2 p) Enantiomers, Diastereomers, Meso

Step 2: Watch Videos
Explained Problems on Proton Guru Channel

Chapter 6

Step 1: Quick Reading
From Organic Chemistry 1 Primer 2018

15 pages to read in the Primer

Lesson I.5 (4 p) Arrow-Pushing

Lesson I.8 (4 p) Applying Arrow-Pushing 

Lesson I.12 (3 p) Equilibrium and Spontaneous Reactions

Lesson I.13 (4 p) Rxn Diagrams and Rates

Step 2: Watch Videos
Explained Problems on Proton Guru Channel

Chapter 7

Step 1: Quick Reading
From Organic Chemistry 1 Primer 2018
Step 2: Watch Videos
Explained Problems on Proton Guru Channel
Note: This chapter covers stability of cations but not of alkenes/radicals. So, you can skip over those problems in Video Lesson I.11 in this Playlist

11 pages to read in the Primer:

Lesson I.11.1 (1 p) Stability of Cations

Lesson III.1 (7 p) Naming Alkenes

Lesson III.2 (3 p) Properties of Alkenes

Chapter 8

Step 1: Quick Reading
From Organic Chemistry 1 Primer 2018

35.5 pages to read in the Primer:

Sounds like a lot, but once you do the 12-page intro, it's only 3-5 pages to learn each reaction with detailed examples.

Lesson I.11.3 (1.5 p) Stability of Alkenes

Lesson III.3-5 (12 p) Hydration and Rxn with HX

Lesson III.6 (5 p) Halogenation and Halohydrins

Lesson III.7 (5 p) Oxymercuration

Lesson III.8 (5 p) Cyclopropanation and Epoxidation

Lesson III.9 (3 p) Hydroboration/Oxidation

Lesson III.10 (4 p) Ozonolysis and Vicinal Diols
 

Step 2: Watch Videos
Explained Problems on Proton Guru Channel

Chapter 9

Step 1: Quick Reading
From Organic Chemistry 1 Primer 2018

21 pages to read in the Primer:

These are all Alkyne Reactions/Naming Alkynes

Lesson III.11 (2 p) Naming Alkynes

Lesson III.12 (5 p) Rxn with X2 or HX

Lesson III.13 (4 p) Reducing Alkyne to Alkane or Alkene

Lesson III.14-15 (7 p) Carbonyl Formation and Tautomers

Lesson III.16 (3 p) Acetylide Anion as a Nucleophile

Step 2: Watch Videos
Explained Problems on Proton Guru Channel

Chapter 10

Step 1: Quick Reading
From Organic Chemistry 1 Primer 2018
Step 2: Watch Videos
Explained Problems on Proton Guru Channel

20 pages to read in the Primer:

Lesson III.18 (4 p) Halogenation of Alkanes

Lesson V.1-2 (6 p) Grignard Reagents and RLi Species*

Lessons V.6-7 (10 p) Pd-Catalyzed Coupling*

*Note: this is usually an organic 2 topic, so it is in Organic Chemistry 2 Primer

Chapter 11

Step 1: Quick Reading
From Organic Chemistry 1 Primer 2018

30 pages to read in the Primer:

Lesson II.2 (4 p) Nucleophiles and Bases

Lesson II.3-5 (9 p) Substitution Rxn of RX

Lesson II.6-9 (10 p) Elimination Rxn of RX

Lesson II.10 (3 p) SN1 SN2 E1 and E2 Compete

Lesson II.11 (4 p) Subst/Elim of ROH

Step 2: Watch Videos
Explained Problems on Proton Guru Channel

Chapter 12

Step 1: Quick Reading
From Organic Chemistry 1 Primer 2018

5 pages to read, then 15 spectra to solve with answers in the Primer:

Lesson VII.3-4 (5 p) Intro to IR Spectroscopy

Lesson VIII.2: Practice IR Solving

Lesson VIII.3: Solutions to IR Practice

Step 2: Watch Videos
Explained Problems on Proton Guru Channel

Chapter 13

Step 1: Quick Reading
From Organic Chemistry 1 Primer 2018
Step 2: Watch Videos
Explained Problems on Proton Guru Channel

9 pages to read, then 15 spectra to solve with answers in the Primer:

Lesson VII.5 (4 p) Intro to NMR Spectrometry

Lesson VII.6(2 p) Carbon-13 NMR Spectrometry

Lesson VII.7 (3 p) Proton NMR Spectrometry

Lesson VIII.4 Practice Proton NMR Solving

Lesson VIII.5 Solutions to Proton NMR Practice

Chapter 14

Step 1: Quick Reading
From Organic Chemistry 1 Primer 2018

16 pages to read in the Primer:

Lesson IV.1 (3 p) Pi Conjugation

Lesson IV.2 (4 p) Addition to Conjugated Dienes

Lesson IV.3 (3 p) Diels-Alder Rxn

Lessons VII.1-2 (6 p) UV/vis Spectroscopy

Step 2: Watch Videos
Explained Problems on Proton Guru Channel

Chapter 15-16: Aromatic Chemistry; These are in Organic 2, which is Coming soon!

Step 2: Watch Videos
Explained Problems on Proton Guru Channel
Step 1: Quick Reading
From Organic Chemistry 1 Primer 2018

X pages to read in the Primer:

Lesson IV

 

Chapter 17

Step 1: Quick Reading
From Organic Chemistry 1 Primer 2018

4 pages to read in the Primer:

Lesson II.12 (1 p) Oxidation and Reduction

Lesson II.13 (3 p) Oxidation of Alcohols

Step 2: Watch Videos
Explained Problems on Proton Guru Channel

Chapter 18

Step 1: Quick Reading
From Organic Chemistry 1 Primer 2018

5 pages to read in the Primer:

Lesson II.14 (3 p) Acid Cleavage of Ethers

Lesson II.15 (2 p) Ring-Opening of Epoxides

Step 2: Watch Videos
Explained Problems on Proton Guru Channel

More Chapters Coming in Time for Organic 2 in Spring 2019!

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