Organic Chemistry

MS 917 - Alcohol and Carbonyl Redox Submitted by Matt on August 6, 2011.

Textbook and Chapter: Carey and Giuliano 8th Ed. (2010), Chapter 15

Keywords: alcohols, hydride reduction, oxidation

Description: Goes over how alcohols can be oxidized to form aldehydes/ketones and carboxylic acids, which can be transformed further using Grignard reagents, hydride reagents such as NaBH4, and by performing Fischer esterification. Includes several synthesis problems involving carbonyls and epoxides. Also includes an NMR based problem.

Total Problems: 5

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MS 916 - Grignard Practice Submitted by Matt on August 6, 2011.

Textbook and Chapter: Carey and Giuliano 8th Ed. (2010), Chapter 14

Keywords: Grignard, nucleophilic acyl addition

Description: Grignard reagent problems: addition to carbonyls (aldehydes, ketones, esters), synthesis, and an NMR problem.

Total Problems: 5

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MS 915 - NMR Practice Submitted by Matt on August 6, 2011.

Textbook and Chapter: Carey and Giuliano 8th Ed. (2010), Chapter 13

Keywords: carbon NMR, proton NMR

Description: Several NMR problems. Two are conceptual and the rest are structure determination.

Total Problems: 7

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MS 914 - Mass Spec Practice Submitted by Matt on August 6, 2011.

Textbook and Chapter: Carey and Giuliano 8th Ed. (2010), Chapter 13

Keywords: alpha cleavage, heterolytic cleavage, homolytic cleavage, mass spec

Description: Goes over alpha-cleavage and the McLafferty rearrangement in mass spectrometry.
(Alpha cleavage is more important to know than the McLafferty rearrangement)

Total Problems: 3

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MS 913 - Benzene EAS Reactions, EDG/EWG, and ortho/meta/para Directors Submitted by Matt on August 6, 2011.

Textbook and Chapter: Carey and Giuliano 8th Ed. (2010), Chapter 12

Keywords: EAS mechanism, EDG and EWG, Friedel-Crafts

Description: Covers electrophilic aromatic substitution (EAS) reactions in detail.

It includes many, many resonance exercises that show why:

  • Electron donating groups (EDG) are ortho-para directors
  • Electron withdrawing groups (EWG) are meta-directors
  • Pyrrole undergoes EAS at C-2 and not C-3
  • Pyridine undergoes EAS at C-3 and not C-2 or C-4
  • Naphthalene undergoes EAS at C-1 and not C-2

Total Problems: 11

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MS 912 - Benzyl Position and Aromaticity Submitted by Matt on August 6, 2011.

Textbook and Chapter: Carey and Giuliano 8th Ed. (2010), Chapter 11

Keywords: aromaticity, benzylic position, heteroaromatic compounds

Description: Goes over benzene, aromaticity, and the benzyl position (1 carbon away from benzene).
Lots of aromatic resonance practice.

Total Problems: 5

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MS 911 - Diels-Alder Practice Submitted by Matt on August 6, 2011.

Textbook and Chapter: Carey and Giuliano 8th Ed. (2010), Chapter 10

Keyword: Diels-Alder

Description: Diels Alder stuff- predict the products, retrosynthesis, and dienophile reactivity.

Total Problems: 5

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MS 909 - Conjugated Dienes and the Allyl Position Submitted by Matt on August 6, 2011.

Textbook and Chapter: Carey and Giuliano 8th Ed. (2010), Chapter 10

Keywords: allylic position, conjugate addition

Description: Covers topics related to the allyl position and conjugated dienes:

  • Allyl cation, anion, and radical resonance forms
  • What conjugated dienes can or can't undergo Diels-Alder reactions
  • Allylic brominations using N-bromosuccinimide (NBS)
  • 1,2 and 1,4 additions (thermodynamic vs kinetic conditions)

Total Problems: 4

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MS 908 - SN1-SN2-E1-E2 Review Submitted by Matt on August 6, 2011.

Textbook and Chapter: Carey and Giuliano 8th Ed. (2010), Chapter 8

Keywords: leaving groups, nucleophilicity, SN1/SN2/E1/E2

Description: Goes through substitution and elimination competition reactions:

  • Nucleophile strength trends
  • Leaving group trends
  • Steric effects
  • How to tell the difference between SN1, SN2, E1, and E2 reaction conditions

Total Problems: 10

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MS 907 - Alkene Addition and Elimination Mechanisms Submitted by Matt on August 6, 2011.

Textbook and Chapter: Carey and Giuliano 8th Ed. (2010), Chapter 6

Keywords: alkene addition, carbocation, dehydration, E1 mechanism

Description: This mendel set is a complement to Carbocation Drills. It is meant to prepare students on how to approach longer and more complicated mechanisms. Reaction mechanisms covered:

  • Acid-catalyzed elimination (dehydration, E1)
  • Acid-catalyzed addition to an alkene
  • Halohydrin formation (halonium ions, which result in anti-additions.)

Total Problems: 4

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