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Organic chemistry: “IUPAC nomenclature”. IUPAC a

Recently, asymmetric synthesis has become a center of attention for synthetic chemists. The use of Raney nickel and tartaric acid was recently reported by Bartok. Reduction of ketone (82) gave alcohols (83) and (84) as a 92:8 mixture in 70% chemical yield. Takeshita et al. also reported an asymmetric reduction of -keto ester (85) to give the corresponding -hydroxy ester (86) in 80% ee (eq 38). In addition, it was found that enantioselectivities were improved by treatment of the Raney nickel with ultrasound prior to use. Blacklock et al. reported an asymmetric reductive amination of -keto ester (88) in which they used the chiral amine (87) instead of a chiral catalyst. The result, shown in eq 39, indicates that the amino ester (89) was produced in 80% yield with 74% de.

Organic chemistry: “IUPAC nomenclature for branched ”

Organic chemistry: “Reactions of and ”. formation through attack of secondary amines on and ; as ; of ; synthesis problems involving . condensation; crossed condensation; condensation. condensation; condensation; crossed condensation; condensation as a route to . ester synthesis; ester synthesis. Michael addition; Michael acceptors; Michael donors

Organic chemistry: “R and S naming”

Organic chemistry: “Introduction to amines”. Amine nomenclature. and of amines. Synthesis of amines—through SN2, through lithium aluminum hydride (LAH) reduction of amides or , through the Gabriel synthesis, or through reductive . Overview of LAH reductions—of and , of carboxylic acids, of esters, of amides, and of .

Organic chemistry: “Hydrolysis of carboxylic acid derivatives”. Hydrolysis of carboxylic acid derivatives ( halides, anhydrides, esters, amides, and ) to form carboxylic acids. attack of alcohols and amines on carboxylic acids and acid derivatives to form esters and amides. Lithium aluminum hydride reduction of and , carboxylic acids, and esters to form alcohols

Organic chemistry: “R and S naming problems”.

Organic chemistry: “More on carboxylic acid derivatives”. attack on carboxylic acid derivatives, including , ester hydrolysis, attack by on esters, amide hydrolysis

Organic chemistry: “Carbohydrates”. Carbohydrates (sugars). D vs. L sugars; . Ring formation; projections; vs. ; vs. . . Glycosides (sugar ). Attack of acetone on sugar units to form cyclic

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Organic chemistry: “Stereochemistry and molecules”

Organic chemistry: “Carboxylic acids and acid derivatives”. Acidity of carboxylic acids; ranking compounds in order of acidity. How to synthesize carboxylic acids: oxidation; carbonation; hydrolysis. The types of carboxylic acid derivative. The general pattern for attack on carboxylic acids and acid derivatives (addition-elimination). . Ranking carboxylic acids derivatives in order of reactivity

Organic chemistry: more on electron-pushing arrows

Organic chemistry: “Carboxylic acids”. Acidity of carboxylic acids; ranking compounds in order of acidity; acid/base reactions with carboxylic acids; extraction (laboratory separation technique). Carbonation (reaction of Grignard reagent with carbon dioxide to form carboxylic acid). Reduction of carboxylic acids with lithium aluminum hydride (LiAlH4, or LAH) to form alcohols. Reaction of carboxylic acids with SOCl2 ( chloride) to form chlorides.

Organic chemistry: SN2 and SN1 reactions

Organic chemistry: “Michael addition. Robinson ”. Michael addition (conjugate addition of ions). Robinson (Michael addition followed by condensation).

Organic chemistry: Three types of SN2 reaction

Organic chemistry: “More on and ”. attack on and ; the three main categories of attack. Two category 1 reactions: attack by a Grignard to form an alcohol; attack by LAH to form an alcohol. A category 2 reaction: attack by alcohol in acidic conditions to form an or . A category 2 “reverse” reaction: reaction of an or with aqueous acid to form an or

Organic chemistry: “SN2, SN1, E2, and E1 reactions”

Organic chemistry: “Introduction to amino acids and peptides”. Biochemistry. How to draw amino acids. Acid/base properties of amino acids. Finding net charge of amino acids and peptides (proteins) at a specified pH. of amino acids and peptides. Peptide (amide) bonds. Amino acid sequencing with partial digestion by enzymes such as . Total acid hydrolysis (TAH)

Organic chemistry: “More on SN2, SN1, E2, and E1 reactions”

Organic chemistry: “ aromatic substitution”. aromatic substitution of benzene. Substitution through intermediates. Summary of methods for synthesis of phenols. oxidation to carboxylic acids; synthesis problems involving oxidation. Radical

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