First year organic chemistry at Bristol

Course details

Course lecturers:
Dr Paul Wyatt (PJW)
Professor Varinder Aggarwal (VKA)
Professor Kevin Booker-Milburn (KIBM)

Recommended textbooks: see my list
Date: October 2007—May 2008.
See also: Wikipedia notes on first year organic chemistry.

Table of contents

  1. Structure and Reactivity (PJW)
    1. Useful links
      1. Wikipedia notes
      2. Terminology
  2. Reactions and Synthesis with Carbonyl Compounds (VKA)
    1. Reactions
      1. Reductions
  3. The Chemistry of Carbon-Carbon Double Bonds (KIBM)
    1. Alkenes
      1. Reactions of alkenes
        1. Electrophilic addition in general
        2. Hydrohalogenation
        3. Hydration
        4. Hydroboration
        5. Bromination
        6. Reduction
        7. Oxidation
    2. Alkynes
    3. Aromatic chemistry

Structure and Reactivity

Useful links

Wikipedia notes

I've compiled a list of Wikipedia articles that cover the topics in this lecture course on my Wikipedia user page: http://en.wikipedia.org/wiki/User:Benjah-bmm27/degree/1/PJW.

Terminology

Much of the terminology used in this course and throughout chemistry (such as electrophile, nucleophile, inductive effects, SN2) came from the late Sir Christopher Kelk Ingold (UCL biography, Wikipedia article), one of the founders of physical organic chemistry.



Reactions and Synthesis with Carbonyl Compounds

Reactions

Reductions

Reduction of carbonyls to alcohols with NaBH4.

Jones oxidation with CrO3.



The Chemistry of Carbon-Carbon Double Bonds

My working for the first KIBM tutorial: download PDF (1.70 MB). Caution — not necessarily 100% correct (although mostly right).

Alkenes

Reactions of alkenes

Electrophilic addition in general
Wikipedia articles: Electrophilic addition, Markovnikov's rule, Syn and anti addition Electrophilic addition in general: March p. 999.
Hydrohalogenation
Wikipedia article: Hydrohalogenation Hydrohalogenation AKA hydro-halo-addition. March pp. 1029–1031.
Hydration
Wikipedia article: Hydration reaction, Oxymercuration reaction Hydration AKA hydro-hydroxy-addition. March pp. 1032–1035
Hydroboration

Wikipedia article: Hydroboration-oxidation reaction Hydroboration, March pp. 1075-1082.


Bromination
Wikipedia articles: Halogen addition reaction, Halonium ion
Bromination AKA dibromo-addition, March pp. 1148-1152.
Reduction
Wikipedia articles: Hydrogenation, Palladium on carbon Hydrogenation AKA dihydro-addition, March pp. 1053-1066 Reduction with H2(g) and a Pd/C catalyst.
Oxidation
Epoxidation
Wikipedia articles: Alkene#Oxidation, Epoxide, meta-Chloroperoxybenzoic acid Epoxidation AKA epi-oxy-addition, March pp. 1169-1179 Epoxidation of an alkene with a peracid is known as the Prilezhaev reaction and its mechanism is sometimes called the Butterfly Mechanism.
Dihydroxylation
Wikipedia articles: Osmium tetroxide#Oxidation of alkenes, Upjohn dihydroxylation Dihydroxylation AKA dihydroxy-addition, March pp. 1162-1168
Ozonolysis
Wikipedia articles: Ozonolysis, Molozonide, Ozonide, 1,3-Dipolar cycloaddition Ozonolysis, March pp. 1736-1742

Synthesis of alkenes


Alkynes


Aromatic chemistry