Test #2 (Chapters 5-8) Study Guide for Organic Chemistry I
Text:  Organic Chemistry, 5th edition, John McMurry
Chapter 5:
5.1 Be able to write one example (book’s are okay) of the four general types of reactions.
5.2 Understand the difference between homolysis and heterolysis (homogenesis vs heterogenesis)
5.3 Know the general steps in the free-radical chlorination of methane.  We will not study many free-radical mechanisms, but this one serves well as a general template.
5.4 Read, then do Spartan-View exercises for fig. 5.2
5.5 Read only (this mechanism is covered in detail later, but you should do the 2 Spartan-Views (Fig’s 5.3 and 5.4, and also check out the OCOL mechanism available at the text website).
5.6 Memorize 4 rules and do all problems on pages 166 and 167.
5.7 Know all equations relating to ?G and rate vs equilibrium (understand difference).
5.8 Be able to calculate ?H as done in prob. 5.11
5.9 Know how to sketch a reaction coordinate diagram (exothermic or endothermic), and where to look for the activation energy and the enthalpy change.
5.10  For a multistep reaction, understand the concept of an intermediate product, and a rate limiting step.  Do prob. 5.14.
Know all keywords on page 181.
Suggested problems:  5.20, 5.21-5.29, 5.38, 5.43…..also try the Spartan-view modeling exercises, 5.48-5.51.
Chapter 6:
6.1 Read
6.2 Calculate DOU for CHONX cpds
6.3 Know IUPAC for simple alkenes, and what a vinyl group is.
6.4 read
6.5-6.6 Recognize and name cis/trans or Z/E geometric isomers of alkenes (just simple ones).
6.7 Why is trans usually more stable than cis alkene?  What is “heat of hydrogenation”, and how can it be used to determine the relative stability of isomeric alkenes?
6.8-6.11 Very improtant!  With careful detail, study and work all examples and practice problems about the electrophilic addition of HBr and HCl to alkenes:  mechanism, Markovnikoff’s rule, carbocation stability, and Hammond’s postulate (early vs late TS).
6.12 Know how and why carbocations rearrange (relative stability of carbocations).
Know all keywords on page 222 and 223.
Suggested problems: 6.24(a,b,f), 6.25, 6.27(a,b,c), 6.30d, 6.32, 6.34, 6.39(a-e), 6.42 (a,d), 6.46, and 6.50.  Also try the molecular modeling exercises 6.56-6.59.
Chapter 7 (The hardest chapter yet. Be careful, reactions and mechanisms contain a lot of detail.)
7.1 Know the two reactions for prep of alkenes on page 233 as reaction tools, but do not study the mechanisms.  The mechanisms will be presented in a later chapter.  Do prob’s 7.1 and 7.2 on page 233.
7.2-7.8 Know the mechanisms for each of these reactions in detail (including any pertinent regiochemistry or stereochemistry associated with a reaction).  Use the OCOL mechanism animations to help visualize the reactions.
7.9-7.10 Read for general knowledge.
Know all keywords on pages 262 and 263.
Create your own set of index cards corresponding to the summary of reactions on pages 263-265, and study the reactions until you can carry them out on any simple alkene starting material.
Suggested problems: 7.23 (a-e), 7.24 (a-e), 7.25 (a-d), 7.30, 7.39 (a,b,d), 7.42 (a-e), and 7.48.
Chapter 8:
8.1-8.2 Read, be able to name simple alkynes by IUPAC (know acetylene).
8.3 Know reaction on page 277 as alkyne prep, but defer mechanism.
8.4 Know how to add HX or halogen to an alkyne, but ignore mechanism on page 279.  Do problem 8.3a,b,c.
8.5 Know this reaction well, including the mechanisms for both “Mark.” And “anti-Mark” hydration.
8.6 Know Cat. Hydrogenation (Alkane is normal product), Li/ammonia (anti addition to produce alkene), and Lindlar’s hydrogenation catalyst (syn addition to produce alkene).
8.7 skip
8.8-8.9 reason for acidity of terminal alkynes, and how they can be used to make new C-C bonds.  Know this well.
8.10 Organic synthesis is the main research activity within organic chemistry.  Read carefully, and do all of the practice problems from page 291 to page 295.  Read “The Art of Organic Synthesis” on pages 295 and 296.
Know all keywords on page 297.
For the summary of reactions on pages 297 to 299, make more index cards to cover all of these reactions, except for 2h (skip)
Suggested problems:  8.18(a,f), 8.19f, 8.21(a,b), 8.23-8.26 (all), 8.28 (a,b,c,d,f), 8.31 (a,b), 8.35, and 8.36.  Also do molecular modeling 8.47 and 8.48.