Leader: Hannah J.
Course: Chem 331
Supplemental Instruction
Instructor: Dr. Winter
Iowa State University
Date: 11/25/15
The following is a (checkable) list of the topics from Ch. 10 and 11 you should know and
understand for Exam 4 and the Final Exam. Where 2 things are listed and one is underlined, the
underlined one is more important.
Ch. 10 & 11 Topics
Ch. 10: Alkyl Halides
 Definition of alkyl halide
 Naming alkyl halides, particularly by the IUPAC naming system (common names are not
required to my knowledge)
 Reaction & Mechanism: Formation of alkyl halides
o Addition of HX or X2 to alkenes (review from ch. 8)
o Addition of HX to a 3˚ alcohol
o Addition of SOCl2 or PBr3 to 1˚ or 2˚ alcohols
o Understand why the preceding 2 reactions work only for the classes listed
 Reaction & Mechanism: Free Radical Halogenation
o Know that nucleophile and electrophile cannot be used to describe radical
reactions
o Mechanism: use single-pronged (fish-hook) arrows and radicals (single electrons,
not lone pairs) and give initiation, propagation, and termination steps (&
understand the meaning/purpose of each of these steps)
o Be able to give mechanisms for both the simple halogenation of methane
(discussed in previous units) and more complicated examples (to produce a
mixture of alkyl halide products—identify major and minor products based on
selectivity of Cl vs. Br)
 Reaction & Mechanism: Allylic bromination
o Also radical reaction
 Allylic vs. Vinyllic Position of alkenes and the stability (& why) of each
o Applies to both radicals and ions (charged species)
 Grignard Reaction & Mechanism (where indicated)
o Purpose: formation of new C-C bonds
o Formation (No mechanism?) and Use (Know mechanism—only with H2O and
D2O?) of Grignard Reagent
 Gilman Reaction & Mechanism (where indicated)
o Purpose: formation of new C-C bonds
o Formation (Know mechanism) and Use (No mechanism) of Gilman Reagent
 Oxidation and Reduction States and (overall) Reactions (based on the electronegativity of
the atom connected to C compared to that of C)
Ch. 11: Nucleophilic Substitution and Elimination
 SN1, SN2, E1, E2 Reactions & Mechanisms
o What these names stand for and the meaning of the names
o Substrate, Solvent, Nucleophile, Leaving Group Preferences of each (see table
summary from class 11/18/15)
o What makes excellent, okay, and poor nucleophiles and examples of each and
how this relates to basicity
1060 Hixson-Lied Student Success Center  515-294-6624  sistaff@iastate.edu  http://www.si.iastate.edu
o Reaction to transform a poor leaving group into an excellent one (sometimes
tosylate) for each class of substrate and desired stereochemistry of the product
o Stereochemistry (inversion, racemic mixture, or loss of stereochemistry) of each
and which mechanisms are concerted & stepwise (and how these qualities are
related)
o Rate law of each reaction and how it relates to substrate, nucleophile (& leaving
group) preferences
o Energy diagram of each reaction type, particularly identification of the ratelimiting step
o Zaitsev’s Rule as it relates to E1 and E2 elimination reactions