Given below is the lecture and lab schedule for the first exam.Be aware that due to variations in the pace at which we cover material our actual schedule may vary.I have indicated below which sections from each chapter we will cover, although the sections may not be covered in the order listed.Note that some material listed for Chapter 9 we covered last semester; you may wish to review it but we won’t be going over it in class.Sections not listed may safely be ignored. I would highly recommend the following approach:

·read all of the indicated material for a particular chapter before we cover it in class

·after each class review the relevant sections in the book

 

Week of:	Mon.	Weds.	Fri.	Lab:	Report:	Due:
Jan. 19	no class	Ch. 9	Ch. 9	No lab.
Jan. 26	Ch. 10	Ch. 10	Ch. 10	Start Project 5.1
Feb. 2	Ch. 10	Ch. 10	Ch. 10	Finish Project 5.1; store product.	Results section; discuss results in recitation Feb. 6	in lab w/o Feb. 9
Feb. 9	Ch. 11	Ch. 11	Ch. 11	Free-Radical Bromination of Hydrocarbons (handout)	yellow pages discuss results in recitation Feb. 13	end of lab
Feb. 16	Ch. 12	Ch. 12	Ch. 12	Nitration of Alkylbenzenes (handout)
Exam I, Chapters 9, 10, 11: Tuesday Feb. 17, 7:00 PM, Trumbower 130
Feb. 23	Ch. 12	Ch. 12	Ch. 12	#22 Alkylation of 1,4-Dimethoxybenzene

 

369	Ch. 9: Electrophilic Addition Reactions of Alkenes and Alkynes
369	The number of sites of unsaturation provides information about the presence of p bonds and rings
370	The reactions of cyclohexene illustrate the fundamental processes of electrophilic addition
372	Addition of HX occurs via a carbocation intermediate generated by the protonation of a p bond
373	Addition of water occurs in the presence of a strong acid that has a nonnucleophilic conjugate base
374	The addition of chlorine or bromine to a p bond occurs by another type of cationic intermediate, a halonium ion
378	Oxymercuration provides an example in which a metal ion is the electrophile
380	Additions to acyclic alkenes occur by the same processes as those observed for cyclohexene
384	Reactions of methylcyclohexene illustrate the regiochemistry associated with electrophilic addition processes
384	Addition of HX occurs to give the product with the proton attached to the less highly substituted carbon – Markovnikov’s rule
387	Addition of bromine and chlorine occurs in a Markovnikov fashion when water is the solvent
390	Oxymercuration further illustrates the generality of Markovnikov addition, in this instance with a metal ion as the electrophile
391	Reactions of an electrophilic reagent with acyclic alkenes also occurs by Markovnikov addition
393	A terminal alkyne reacts with electrophiles in sequential reactions by Markovnikov addition
394	The Markovnikov addition of water to an alkyne is catalyzed by mercury (II) ion with sulfuric acid and produces a ketone
396	Electrophilic addition to an internal alkyne gives a mixture of products unless the addend or alkyne is symmetric
397	A diene undergoes 1,2- and 1,4-addition processes, illustrating the concepts of kinetic versus thermodynamic control
399	Carbocations can add to alkenes to form dimers, illustrating the Markovnikov addition of the electrophile R+ to a double bond
401	Alkenes dimerize in biological systems by electrophilic addition to create new carbon-carbon bonds
403	Polymerization occurs via carbocation addition to an alkene in a Markovnikov fashion
405	Intramolecular addition of a carbocation to a p bond produces a ring
407	Steroids are made by successive cyclization reactions starting from squalene
409	Summary
415	Ch. 10: Concerted Addition Reactions of Alkenes and Alkynes
416	Hydrogen adds stereospecifically to carbon-carbon double or triple bonds in the presence of a metal catalyst
419	Hydroboration provides a useful way to functionalize carbon-carbon double and triple bonds
421	Hydroboration is a stereospecific and regioselective reaction occurring via a four-membered ring transition state
424	Organoboranes react with certain nucleophiles to yield functionalized alkanes
425	Hydroperoxide ion converts an organoborane to an alcohol
431	A cycloaddition process called the Diels-Alder reaction is used to prepare six-membered rings
433	Molecular orbitals of a diene and dienophile must have the proper symmetry to react
438	The regio- and stereoselectivity of the Diels-Alder reaction is dependent upon the substitution pattern of the diene and dienophile
440	Ozonolysis of an alkene cleaves the carbon-carbon p bond, yielding carbonyl-containing compounds
442	Potassium permanganate and osmium tetroxide react with alkenes to form metalate esters, also by a formal [4+2] cycloaddition process
447	An epoxide is formed by the reaction between a peracid and an alkene
454	Summary
465	Ch. 11: Free Radicals: Substitution and Addition Reactions
466	Chlorination of methane occurs via a radical chain process
468	Bond dissociation energies can be used to calculate or estimate free energy changes of radical reactions
469	Chlorination of alkanes leads to mixtures of isomeric products
473	Bromination of an alkane is more selective than chlorination
474	N-bromosuccinimide provides a low concentration of bromine for the free-radical reactions of allylic and benzylic substrates
477	Allylic oxidation is an important biological process for generating potent physiologically active compounds
482	Metal ions are used in several ways to generate radicals in biological systems
485	An alkyne can be reduced by an alkali metal in liquid ammonia
486	Hydrogen bromide adds to alkenes via a radical process with apparent anti-Markovnikov regiochemistry
489	Addition of an alkyl radical to an alkene provides a general method for the preparation of polymers
491	Copolymers are formed by the addition of radicals to more than one monomer
492	Branched polymers result from hydrogen-atom transfer processes
499	The cyclic pathway of arachidonic acid metabolism produces prostaglandins via a radical ring-forming process
501	A tandem cyclization can occur when there is more than one point of unsaturation
503	Enediynes are potent anticancer drugs that react by forming a diradical that subsequently cleaves DNA
506	Summary