Week  of:	Mon.	Weds.	Fri.	Lab	Report	Due
				Grignard report (abstract, results, conclusions) due in lab week of April 26
April 19	20	20	21	Project 12.1, continued: work up benzoin condensation, characterize product	see below
				Exam III: Tues. April 20
April 26	21	21	22	Project 12.2: Sodium Borohydride Reduction of Benzoin do borohydride reduction. characterize product	yellow pages and spectra	in lab, week of May 3
May 3	23	24	no class	Clean up and check out
				Final Exam: Mon. May 10, 12:00

Note the change in the due date for the Grignard report.

For the week of April 19 we will be working up the product from the benzoin condensation.You will recrystallize the crude product as described in the text, and characterize the product by melting point, IR, and NMR.The following week, in place of the previously scheduled experiment, we will be doing the borohydride reduction of the benzoin you prepared (Project 12, part 2).You will characterize the crude product by melting point and NMR, with the goal being to determine the ratio of stereoisomers formed.You will not do the last part of the project (the acetal synthesis). Your report for the entire Project 12 will be your yellow pages, turned in the last lab period, supplemented by your spectra.This will constitute the “notebook” portion of your lab grade for the semester, so do a good job.

 

979	Ch. 20: The Acid-Base Chemistry of Carbonyl Compounds
980	The acidity of carboxylic, sulfonic, and phosphoric acids results from resonance stabilization of the corresponding anion
982	Variations in acidity can be rationalized by the influence of inductive effects
984	Inductive effects can be used to rationalize the acid strengths of benzoic acid derivatives
984	Dicarboxylic acids have two acidic protons
986	An amide is more acidic than an amine because of resonance stabilization of the conjugate base
987	A ketone is more acidic than an alkane because its conjugate base is stabilized by resonance
988	An enolate ion is the conjugate base of an enol, a derivative of a carbonyl compound that is formed by tautomerism
991	Isomerization reactions of carbonyl compounds occur via enol and enolate derivatives
993	Ketones undergo halogenation at the alpha position via an enolate
996	A strong base facilitates complete conversion of a carbonyl compound to its enolate derivative
997	An unsymmetric ketone can form two different enolate ions
999	A ketone enolate reacts with an alkyl halide via an SN2 process
1007	The enolate of an ester is also a potent nucleophile
1009	The carbanion derivative of a carboxylic acid is readily generated and can function as a nucleophile
1011	The presence of two electron-withdrawing groups increases the acidity of the alpha hydrogen atoms substantially
1016	A carboxylic acid functionality beta to a carbonyl; group undergoes facile decarboxylation
1020	Decarboxylation of beta-keto acids is an important metabolic transformation in biology
1021	Decarboxylation of a beta-keto acid can be coupled to other processes
1024	Summary
1033	Ch. 21: Nucleophilic Addition Reactions of Enolate Ions with Carbonyl Groups
1034	The aldol reaction is the self-condensation of aldehydes
1035	Dehydration of the aldol product occurs by an E1cb mechanism
1037	The retroaldol reaction leads to cleavage of a carbon-carbon bond
1038	Ketones can undergo the aldol reaction
1038	The mixed-aldol reaction creates a mixture of products
1040	The crossed-aldol reaction is practical when one component lacks a proton alpha to the carbonyl group
1045	The addition of an ester enolate to an aldehyde or ketone constitutes a variant of the directed-aldol reaction
1046	The metabolism of glucose makes use of a retroaldol process
1052	The biosynthesis of D-glucose (gluconeogenesis) makes use of an aldol reaction catalyzed by an enzyme called transaldolase
1056	Aldolase can be used to synthesize carbohydrates in the laboratory
1058	A thioester enolate ion condenses with a ketone in the citric acid cycle to produce a carbon-carbon bond
1059	Esters undergo the Claisen condensation in a manner similar to the aldol reaction
1061	Formation of a resonance-stabilized carbanion drives the Claisen condensation to completion
1063	The Dieckmann cyclization is an intramolecular Claisen condensation
1064	The crossed-Claisen condensation couples different esters
1067	A ketone can function as one of the reaction components in the crossed-Claisen condensation
1068	Carboxylation is a variant of the crossed-Claisen condensation
1069	Biological carboxylations make use of the coenzyme biotin
1073	The retro-Claisen condensation is important for degrading fatty acids in living systems
1078	The biosynthesis of fatty acids uses the Claisen condensation
1082	Ketone bodies are synthesized by a combination of Claisen, aldol, and retroaldol reactions
1087	Summary
1097	Ch. 22: Nucleophilic Addition to a,b-Unsaturated Carbonyl Compounds
1098	An a,b-unsaturated carbonyl compound is the product of several transformations
1103	Addition of water by conjugate addition is the reverse of the E1cb mechanism
1105	Conjugate addition of water defines key steps in fatty acid metabolism and in the citric acid cycle
1113	Drug detoxification occurs via formation of conjugates
1115	The Michael reaction is a conjugate addition reaction that involves an active methylene compound
1117	Unstabilized enolate ions can undergo the Michael reaction
1127	Tandem addition-alkylation is important for the biosynthesis of thymidine
1130	Some antitumor drugs undergo a Michael reaction with thymidylate synthase and inhibit the synthesis of thymidine
1137	Summary
1151	Ch. 23: The Chemistry of Amines and Other Nitrogen-Containing Compounds
1153	The basicity of an amine, like the acidity of a carboxylic acid, is influenced by both inductive and resonance effects
1156	Some nitrogen-containing compounds are acidic
1157	Pyramidal inversion of nitrogen influences the stereochemistry of amines and derivatives
1158	An amine is a nucleophile in substitution processes
1162	As a nucleophile, an amine can add to p-bonds
1164	Penicillin functions as an antibiotic by undergoing nucleophilic addition to the b-lactam carbonyl group
1165	Polyamides are prepared from dicarboxylic acids and diamines or from amino acids
1193	Summary
1205	Ch. 24: The Chemistry of Heterocyclic Compounds
1206	Except for heterocycles that have a three- or four-membered ring, cyclic compounds have properties like their acyclic compounds
1207	Pyridine is a heterocyclic analog of benzene that can function as a base and as a nucleophile
1210	Pyridine undergoes electrophilic substitution reactions with great difficulty
1212	Pyridine reacts more like a carbonyl compound than an aromatic compound
1216	Some pyridine derivatives react with nucleophiles by a conjugate addition process
1217	Addition of hydride ion to the pyridine ring is the basis for many reduction processes in biological systems
1223	Pyrrole is weakly basic but has substantial aromatic character
1227	Pyrrole is extremely reactive toward electrophilic aromatic substitution processes
1231	Furan and thiophene also undergo facile electrophilic aromatic substitution
1232	Indole is a fused-ring derivative of pyrrole that constitutes the side chain of the amino acid tryptophan
1234	Azoles are aromatic compounds that have two heteroatoms in a five-membered ring
1238	An alkylated thiazole ion is an important constituent of thiamine
1239	TPP is an important coenzyme for the decarboxylation of a-ketoacids
1243	TPP also catalyzes the conversion of pyruvate to acetyl coenzyme A
1246	Thiamine can stabilize a nucleophilic center that is used to create a carbon-carbon bond
1250	Summary