About 70-75% of the exam will be on material from the first three hour tests:
Determine the hybridization of the sigma bonds, and the geometry about an atom from its Lewis structure.
Distinguish between primary, secondary, and tertiary carbon atoms.
Draw structures from names of alkanes, alkenes, alkynes, and aromatic compounds, including special names such as aniline, phenol, toluene, styrene, etc.
Name compounds in these classes from their structures.
Be able to name and draw the common alkyl radicals (Table 19.3).
Given a compound, determine its structural and geometric isomers.
Be able to draw the products of reaction of alkenes and alkynes with halogens, KMnO4, HCl, HBr, and HOH, including deciding which is the major product if there are two possibilities. Markovnikov's rule.
Draw the product of reaction of alkyl benzene with KMnO4.
Drawing monomers from polymer structure, both addition polymers and condensation polymers..
Drawing a polymer section from a monomer structure, both addition polymers and condensation polymers..
Names and structures of a few common addition polymers. (polyethylene, polypropylene, polyvinyl chloride, polystyrene, teflon, polyisoprene, polybutadiene).
Naming alcohols from a structure; drawing a structure from a name. (Common and IUPAC names--Table 22.1)
Distinguishing primary, secondary, and tertiary alcohols; Oxidation reactions of these three types.
Dehydration of alcohols; Saytzeff's rule.
Naming ethers from a structure (common name: as alkyl or aryl ether; IUPAC name: as alkoxy alkane; Examples Table 22.5); Drawing structure from name.
Williamson synthesis of ethers.
Identifying oxidation reduction reactions: identifying the reactant being oxidized and the reactant being reduced.
Naming aldehydes and ketones from structure; drawing a structure from a name. (Common and IUPAC names for ketones).
Color tests for aldehydes: Tollens, Fehlings, and Benedicts tests. Know oxidizing reagent in each, and the products in the test.
Reduction of aldehydes and ketones to alcohols. (H2 and a catalyst, LiAlH4, NaBH4 )
Addition reactions to aldehydes and ketones: formation of hemiacetals, hemiketals, acetals, ketals, cyanohydrins, aldol self-condensation products.
IUPAC and common names of acids (including diacids through adipic acid and aromatic acids), esters, and the alcohol component of the esters. Be able to draw a structure from a name, or name a structure from a drawing.
Preparation of acids by oxidation of alcohols (primary only) and aldehydes,
oxidation of alkyl benzenes, and hydrolysis of esters, amides, and nitriles.
Preparation of acid chlorides and acid anhydrides. Reaction of these derivatives
with alcohols to form esters and amines or with ammonia and amines to form
Formation of polyesters. Examples of a polyester repeating structure.
Products of acid and alkaline hydrolysis of esters, including charge and protonated state of the products.
General structure of fats and oils, and the differences between these two general classes.
Formation and properties of soaps. General features of detergents.
IUPAC and common names of amides and their amine and acid components, including special names for aromatic amides and aromatic amines. Be able to draw a structure from a name, or name a structure from a drawing.
Products of acid and alkaline hydrolysis of amides, including charge and protonated state of the products.
Formation of polyamides. Examples of a polyamide repeating structure. Structures of nylon-66 and nylon-6.
Classification of amines (primary, secondary, tertiary).
Preparation of amines by alkylation (reaction with alkyl halides) of ammonia
or of amines.
Prepartion of amines by reduction of amides, nitriles, and aromatic nitro compounds.
Basic property of amines: reaction with strong acids and with water. Name
the ammonium salts formed.
Reaction of amines with acid chlorides or anydrides to form amides.
Identifying acid base reactions: identifying the acid and base in the reactants and the conjugate acid and base in the products.
Given the pKa values of acids, predict the direction and extent of an acid-base reaction.
About 25-30% of the exam will be on the following material covered since Test 3.
Identifying chiral carbons in a complex molecule, including one drawn in a line structure. (Look at slide 23, Chapter 26, again).
Identifying the relationship between different Fischer projections of the same chiral compound. (pages 724, 725; slides 27 and 28, Chapter 26).
Distinguishing enantiomers, diastereoisomers, and meso structures for compounds with two chiral centers. (pages 728, 729; slides 29-33, Chapter 26).
Isomeric relationship between sugars (enantiomer, epimer, diastereomer, structural isomer).
Drawing structures of glucose and galactose in the open Fischer projection, and the alpha or beta forms of these sugars in the Haworth projection.
Structure of amylose, amylopectin, glycogen, and cellulose (i.e., how are the sugar units connected in each)..
Nomenclature of Fatty Acids (Slides 12-16), including short hand notation (example: 9,12-C18:2), IUPAC name (example: 9,12-octadecadienoic acid), common name (example: linoleic acid) and omega class (example: omega-6).
Action of some eicosanoids and their inhibitors(slide 18 and 19--by name, not structure).
Fats and oils, structure and saponification. Olestra structure and use.
Recognize the structure of a phospholipid, sphingolipid, wax, and steroid.
Explain the difference between a spherical micelle and a bilayer structure when lipids aggregate in water.