Download Types of reactions you know:

REVIEW OF CHEM 331 REACTIONS:
Reactions should be the thing you study first, since they are important in not only the
reaction section, but also in mechanisms and synthesis. Studying reactions also pays off,
since you will be expected to know these in 332.
How to use this worksheet:
--Fill in the bolded parts during SI
--When you are studying, you can use the rest of the points to find reactions that fit the
description. There are a lot of words on here—draw the reactions that I’ve written about.
Types of reactions you know:
1) Reactions of double bonds (and sometimes triple bonds)
a. Adding 2 things across a double bond
b. Formation of a double bond
c. Adding to the carbon next to a double bond (NBS, CCl4)
d. Cleavage at the double bond
e. Special things that pertain to conjugated double bonds:
i. 1,2 and 1,4 products
ii. Diels-Alder
2) Light-induced reactions
a. Chlorination or bromination
b. NBS/hv
3) SN1/SN2/E1/E2
4) Organometallic Reactions
a. Grignard
b. CuLi
It’s sometimes helpful to group reactions according to what they are useful for in
synthesis:
1) Adding alkyl groups – if the product has more carbons than the starting
material.
a. Add a primary alkyl halide to a terminal alkyne (an SN2 rxn)
b. CuLi and alkyl halide (use this if you need to add to the middle of a
chain)
2) Stereospecific reactions
a. SN2 – inverts R/S configuration
b. Reduction of a triple bond to a double bond
i. Li/NH3 vs. Lindlar
c. Markovnikov/anti-Markovnikov reactions
d. Reactions with a bromonium intermediate will add anti
3) Reactions that create certain functional groups
a. Carbonyls
i. Cleavage reactions (double bonds, triple bonds, diols)
b. Three-membered rings
i. Epoxides (by peroxides, acids, and bases)
ii. Cyclopropanes (Simmons-Smith and addition of CHCl3)
c.
d.
e.
f.
g.
Triple bonds
Double bonds
Halides from hydrocarbons (light-induced reactions)
Alcohols
Cyclohexanes (Diels Alder)
Practicing Reactions:
--A helpful resource is the companion website for the 6th edition of your textbook.
Google “McMurrray Organic Chem” and it should be the first hit. I will also have a link
on the SI website to the website. The “organic interactive” problems in each chapter are
extremely helpful. Even if you don’t use this to study for the final, it is a good quick and
easy review after your o-chem-less summer months. 
--Make notecards! Study them!
--You have more than just the old finals at your disposal—you can practice reactions off
of any of the old exams 1 through 5.
Mechanisms you know:
1) Reactions that have a carbocation intermediate (these follow Markovnikov’s rule
and are subject to rearrangement through resonance)
a. Addition of HX to double bonds
b. SN1/E1 reactions (especially when water or an alcohol is used)
2) Reactions with a radical intermediate
a. Any light-induced reactions (Cl2, Br2, or NBS and hv)
b. Know initiation/propagation/termination steps
Intermediates and transition states you know:
1) Carbocations (see list of reactions above)
2) Radicals (see above)
3) SN2/SN1/E1/E2 reactions
4) Bromonium ions (addition of Br2 or Br2 and H2O)