Figure Number: 17-00CO Title: Penicillin G Caption: Ball-and-stick model of penicillin G. Notes: Penicillin has a carbonyl group located in a four-membered ring. The ring strain makes this carbonyl exceptionally unstable and reactive.

Figure Number: 17-00-02UN Title: Carbonyl Compounds Caption: Ball-and-stick models of several different kinds of carbonyl compounds: an acyl chloride, an ester, a carboxylic acid, and an amide. Notes: The presence or absence of a carbonyl group differentiates esters from ethers, carboxylic acids from alcohols, acyl halides from halides, and amides from amines.

Figure Number: 17-01 Title: Figure 17.1 Caption: Orbital picture of C–O bonding in a carbonyl group. Notes: The first bond between carbon and oxygen in a carbonyl group is created by overlapping an sp2 hybrid orbital from carbon with an sp2 hybrid orbital from oxygen (sigma bond). The second bond between carbon and oxygen is created by overlapping a p orbital from carbon with a p orbital from oxygen (pi bond). The two remaining sp2 hybrid orbitals on oxygen are used to hold oxygen's lone pairs.

Figure Number: 17-02 Title: Figure 17.2 Caption: Reaction coordinate diagrams for nucleophilic acyl substitution reaction in which the nucleophile is a stronger base, weaker base, and equally strong base relative to the leaving group. Notes: Nucleophilic acyl substitution reactions go spontaneously in the direction in which the stronger base is consumed as the nucleophile, and the weaker base is generated as the leaving group. TI designates the tetrahedral intermediate in these diagrams.

Figure Number: 17-03 Title: Figure 17.3 Caption: MO diagram and schematic showing attack of a nucleophile on a carbonyl group. Notes: Since electrons generally move from the HOMO of one reaction center into the LUMO of the other reaction center, the base (nucleophile) generally moves electrons from its HOMO (nonbonding orbital on nitrogen) toward the electrophile's LUMO (carbonyl p* antibonding orbital). These orbitals overlap, forming a sigma bond.

Figure Number: 17-03-14UN Title: Acetyl Chloride Caption: Ball-and-stick model of acetyl chloride. Notes: Acetyl chloride is a strongly electrophilic substance with a very stable leaving group (chloride).

Figure Number: 17-03-29UN Title: Acetic Anhydride Caption: Ball-and-stick model of acetic anhydride. Notes: Anhydrides are electrophilic substances which generate stable leaving groups (carboxylate anions) when they react with nucleophiles. Anhydrides are not as electrophilic as acid chlorides because acid chlorides generate more stable leaving groups (chloride ions) when they react with nucleophiles.

Figure Number: 17-03-34UN Title: Methyl Acetate Caption: Ball-and-stick model of methyl acetate. Notes: Methyl acetate is an ester. Esters are mild electrophiles which react with strong nucleophiles to generate mildly unstable leaving groups (alkoxide ions). Esters are less electrophilic than acid halides and anhydrides because they generate less stable leaving groups when they react with nucleophiles.

Figure Number: 17-04 Title: Figure 17.4 Caption: Schematic diagram of a micellar mixture. Notes: Space-filling water molecules are shown interacting with polar carboxylate head groups of soap molecules on the outside surface of a micelle, while the nonpolar hydrocarbon tails of the micelle interact with one another to form a water-excluding (hydrophobic) sphere.

Figure Number: 17-04-03UN Title: Acetic Acid Caption: Ball-and-stick model of acetic acid. Notes: Carboxylic acids are mild electrophiles which react with strong nucleophiles to generate mildly unstable leaving groups (hydroxide ions). Carboxylic acids are less electrophilic than acid halides and anhydrides because they generate less stable leaving groups when they react with nucleophiles. They have comparable reactivity to esters.

Figure Number: 17-04-10UN Title: Acetamide Caption: Ball-and-stick model of acetamide. Notes: Acetamide is an amide. Amides are relatively poor electrophiles because they generate unstable leaving groups (amide anions) when attacked by nucleophiles. Amides are weaker electrophiles than acid halides, anhydrides, esters, and carboxylic acids.

Figure Number: 17-05-014UN Title: Acetonitrile Caption: Ball-and-stick model of acetonitrile. Notes: Nitriles are even less electrophilic than amides (and therefore less electrophilic than acid halides, anhydrides, esters, and carboxylic acids). Nitriles can be hydrolyzed to carboxylic acids in acidic water with heat. Amides are formed as intermediates in this process.

Figure Number: 17-05-092P52 Title: End-of-Chapter Problem 52 Caption: Infrared spectra associated with end-of-chapter Problem 52. Notes: Compounds A and B are obtained by reacting 1-bromobutane with ammonia. Compound A reacts with acetyl chloride to form compound C (see IR in figure). Compound B reacts with acetyl chloride to form compound D (see IR in figure). Identify A, B, C, and D.

Figure Number: 17-05-103P56 Title: End-of-Chapter Problem 56 Caption: Proton NMR spectrum associated with end-of-chapter Problem 56. Notes: The proton NMR spectrum shown in the figure is of a compound which is created when a precursor with the molecular formula C4H6Cl2O reacts with one equivalent of methanol. Identify the precursor to the compound responsible for the NMR spectrum.

Figure Number: 17-05-105P60 Title: End-of-Chapter Problem 60 Caption: Proton NMR spectrum associated with end-of-chapter Problem 60. Notes: The proton NMR spectrum shown in the figure is of a compound which is created when a precursor with the molecular formula C11H14O2 undergoes acid-catalyzed hydrolysis. Identify the precursor to the compound responsible for the NMR spectrum.

Figure Number: 17-05-107P63 Title: End-of-Chapter Problem 63 Caption: Proton NMR spectra associated with end-of-chapter Problem 63. Notes: The proton NMR spectra shown are generated by two isomeric esters which have the molecular formula C8H8O2. Determine the structures of the two esters and decide which ester will hydrolyze more completely at equilibrium in a pH 10 (basic) aqueous solution.

Figure Number: 17-TB01 Title: Table 17.1 The pKa Values of the Conjugate Acids of the Leaving Groups of Carbonyl Compounds Caption: Notes:

Figure Number: 17-TB02 Title: Table 17.2 Structures, Names and pKa Values of Some Simple Dicarboxylic Acids Caption: Notes: