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
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 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
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
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
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
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 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
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
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
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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
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
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
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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
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
X pages to read in the Primer:
Lesson IV
Chapter 17
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
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!