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Chapter 17
Carbonyl Compounds I

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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.
Keywords
penicillin, G, ball-and-stick, carbonyl, reactive, four-membered, ring
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.
Keywords
penicillin, G, ball-and-stick, carbonyl, reactive, four-membered, ring
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.
Keywords
carbonyl, compounds, acyl, chloride, ester, carboxylic, acid, amide
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.
Keywords
figure, 17.1, bonding, carbonyl, orbitals
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.
Keywords
figure, 17.2, reaction coordinate, diagrams, nucleophilic, acyl, substitution
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.
Keywords
figure, 17.3, MO, diagram, attack, nucleophile, carbonyl
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).
Keywords
ball-and-stick, acetyl, chloride
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.
Keywords
acetic, anhydride, ball-and-stick
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.
Keywords
methyl, acetate, esters, ball-and-stick
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.
Keywords
figure, 17.4, micelles
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.
Keywords
acetic, acid, ball-and-stick, carboxylic, acid
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.
Keywords
ball-and-stick, acetamide, amide, electrophiles
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.
Keywords
ball-and-stick, acetonitrile, nitriles, electrophilic
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.
Keywords
problem, 52, IR, spectra, 1-bromobutane, ammonia
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.
Keywords
end-of-chapter, problem, 56
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.
Keywords
end-of-chapter, problem, 60
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.
Keywords
end-of-chapter, problem, 63
17-TB01
Title
Table 17.1 The pKa Values of the Conjugate Acids of the Leaving Groups of Carbonyl Compounds
Caption
Notes
Keywords
17-TB02
Title
Table 17.2 Structures, Names and pKa Values of Some Simple Dicarboxylic Acids
Caption
Notes
Keywords

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