- 18.20P: ?What aldol addition product is formed from each of the following c...
- 18.21P: For each of the following compounds, indicate the aldehyde or keton...
- 18.22P: Give the product obtained from the aldol condensation of cyclohexan...
- 18.23P: ?How could you prepare the following compounds using a starting mat...
- 18.24P: ?Describe how the following compounds could be prepared using an al...
- 18.25P: ?What two carbonyl compounds are required for the synthesis of mora...
- 18.26P: ?Propose a mechanism for the following reaction:
- 18.28P: ?Which of the following esters cannot undergo a Claisen condensation?
- 18.27P: ?Draw the products of the following reactions:
- 18.29P: ?Draw the product of each of the following reactions:
- 18.30P: ?Show how each of the following compounds could be prepared from me...
- 18.31P: Write the mechanism for the base-catalyzed formation of a cyclic ?-...
- 18.32P: If the preference for formation of a six-membered ring were not so ...
- 18.33P: Can 2,4-pentanedione undergo an intramolecular aldol addition? If s...
- 18.34P: ?Draw the product of the reaction of each of the following compound...
- 18.35P: ?Draw the product obtained by heating each pair of ketones in a bas...
- 18.36P: ?What two carbonyl compounds are needed to synthesize each of the f...
- 18.37P: ?Which of the following compounds would be expected to decarboxylat...
- 18.38P: What alkyl bromide(s) should be used in the malonic ester synthesis...
- 18.40P: What alkyl bromide should be used in the acetoacetic ester synthesi...
- 18.42P: Design a synthesis for each of the following compounds using the gi...
- 18.39P: ?Explain why the following carboxylic acids cannot be prepared by a...
- 18.43P: Propose a mechanism for the formation of fructose-1,6-diphosphate f...
- 18.44P: Palmitic acid is a straight-chain saturated 16-carbon fatty acid. H...
- 18.45P: a. If the biosynthesis of palmitic acid were carried out with CD3CO...
- 18.46P: When the enzymatic decarboxylation of acetoacetate is carried out i...
- 18.47P: Draw a structure for each of the following:a. ethyl acetoacetateb. ...
- 18.48P: Draw the products of the following reactions:a. diethyl heptanedioa...
- 18.49P: ?Number the following compounds in order of increasing \(\mathrm{pK...
- 18.50P: The 1H NMR chemical shifts of nitromethane, dinitromethane, and tri...
- 18.51P: ?Which of the following compounds decarboxylates when heated?
- 18.52P: Draw the products of the following reactions:a. 1,3-cyclohexanedion...
- 18.53P: A racemic mixture of 2-methyl-1-phenyl-1-butanone is formed when (R...
- 18.54P: ?Draw the products of the following reactions:
- 18.55P: ?What is the product of the following reaction?
- 18.56P: An aldol addition can be catalyzed by acids as well as by bases. Pr...
- 18.58P: ?Identify A–L. ( Hint: A shows three singlets in its \({ }^{1} \mat...
- 18.57P: ?In the presence of excess base and excess halogen, a methyl ketone...
- 18.59P: Using cyclopentanone as the reactant, show the product ofa. acid-ca...
- 18.60P: ?Show how the following compounds could be prepared from cyclohexan...
- 18.61P: ?A \(\beta, \gamma\) -unsaturated carbonyl compound rearranges to a...
- 18.62P: ?There are other condensation reactions similar to the aldol and Cl...
- 18.63P: ?The Reformatsky reaction is an addition reaction in which an organ...
- 18.64P: ?The ketone whose \({ }^{1} \mathrm{H}\) NMR spectrum is shown here...
- 18.65P: ?Indicate how the following compounds could be synthesized from cyc...
- 18.66P: ?Compound A with molecular formula \(\mathrm{C}_{6} \mathrm{H}_{10}...
- 18.67P: ?Indicate how each of the following compounds could be synthesized ...
- 18.68P: ?Draw the products of the following reactions:
- 18.69P: ?Show how the following compound can be prepared from starting mate...
- 18.70P: a. Show how the amino acid alanine can be synthesized from propanoi...
- 18.71P: ?A student tried to prepare the following compounds using aldol con...
- 18.72P: ?Show how the following compounds could be synthesized. The only ca...
- 18.73P: ?Explain why the following bromoketone forms different bicyclic com...
- 18.74P: ?A Mannich reaction puts a group on the a -carbon of a carbon acid....
- 18.75P: ?What carbonyl compounds are required to prepare a compound with mo...
- 18.76P: ?Ninhydrin reacts with an amino acid to form a purple-colored compo...
- 18.77P: ?A carboxylic acid is formed when an \(\alpha\)-haloketone reacts w...
- 18.78P: ?An \(\alpha, \beta\) -unsaturated carbonyl compound can be prepare...
- 18.80P: ?A Cannizzaro reaction is the reaction of an aldehyde that has no \...
- 18.79P: a. What carboxylic acid would be formed if the malonic ester synthe...
- 18.81P: ?Propose a reasonable mechanism for each of the following reactions:
- 18.82P: ?The following reaction is known as the benzoin condensation. The r...
- 18.84P: ?Propose a mechanism for the following reaction. ( Hint: The interm...
- 18.85P: ?A compound known as Hagemann’s ester can be prepared by treating a...
- 18.86P: ?Amobarbital is a sedative marketed under the trade name Amytal. Pr...
- 18.87P: ?Propose a reasonable mechanism for the following reaction:
- 18.83P: ?Orsellinic acid, a common constituent of lichens, is synthesized f...
- 18.1P: ?Explain why the \(p K_{a}\) of a hydrogen bonded to the \(s p^{3}\...
- 18.2P: Give an example for each of the following:a. a ?-keto nitrile b. a ...
- 18.3P: ?Explain why a base can remove a proton from the a -carbon of \(N\)...
- 18.4P: Explain why the ?-hydrogen of an N,N-disubstituted amide is less ac...
- 18.5P: ?List the compounds in each of the following groups in order from s...
- 18.6P: Explain why 92% of 2,4-pentanedione exists as the enol tautomer in ...
- 18.7P: ?Draw the enol tautomers for each of the following compounds. For c...
- 18.8P: When a dilute solution of acetaldehyde in D2O containing NaOD is sh...
- 18.9P: Explain why a racemic mixture is formed when (R)-4-methyl-3-hexanon...
- 18.10P: A ketone undergoes acid-catalyzed bromination, acid-catalyzed chlor...
- 18.11P: ?Show how the following compounds could be prepared from the given ...
- 18.12P: What compound is formed when a dilute solution of cyclohexanone is ...
- 18.13P: Explain why alkylation of an a-carbon works best if the alkyl halid...
- 18.14P: ?How could each of the following compounds be prepared from a keton...
- 18.15P: ?How many stereoisomers are obtained from each of the syntheses des...
- 18.16P: ?How could each of the following compounds be prepared from cyclohe...
- 18.17P: ?Describe how the following compounds could be prepared from cycloh...
- 18.19: ?What reagents should be used to prepare the following compounds?
- 18.18P: ?Draw the products of the following reactions:
- 18.47: Draw a structure for each of the following: a. ethyl acetoacetate b...
- 18.48: Draw the products of the following reactions: a. diethyl heptanedio...
- 18.49: Number the following compounds in order of increasing p Ka value. (...
- 18.50: The 1 H NMR chemical shifts of nitromethane, dinitromethane, and tr...
- 18.51: Which of the following compounds decarboxylates when heated?
- 18.52: Draw the products of the following reactions: a. 1,3-cyclohexanedio...
- 18.53: A racemic mixture of 2-methyl-1-phenyl-1-butanone is formed when ( ...
- 18.54: Draw the products of the following reactions:
- 18.55: What is the product of the following reaction?
- 18.56: An aldol addition can be catalyzed by acids as well as by bases. Pr...
- 18.57: In the presence of excess base and excess halogen, a methyl ketone ...
- 18.58: Identify AL. ( Hint: A shows three singlets in its 1 H NMR spectrum...
- 18.59: Using cyclopentanone as the reactant, show the product of a. acid-c...
- 18.60: Show how the following compounds could be prepared from cyclohexanone:
- 18.61: A b , g -unsaturated carbonyl compound rearranges to a more stable ...
- 18.62: There are other condensation reactions similar to the aldol and Cla...
- 18.63: The Reformatsky reaction is an addition reaction in which an organo...
- 18.64: The ketone whose 1 H NMR spectrum is shown here was obtained as the...
- 18.65: Indicate how the following compounds could be synthesized from cycl...
- 18.66: Compound A with molecular formula C6H10 has two peaks in its 1 H NM...
- 18.67: Indicate how each of the following compounds could be synthesized f...
- 18.68: Draw the products of the following reactions:
- 18.69: Show how the following compound can be prepared from starting mater...
- 18.70: a. Show how the amino acid alanine can be synthesized from propanoi...
- 18.71: A student tried to prepare the following compounds using aldol cond...
- 18.72: Show how the following compounds could be synthesized. The only car...
- 18.73: Explain why the following bromoketone forms different bicyclic comp...
- 18.74: A Mannich reaction puts a NCH2 R R group on the a -carbon of a carb...
- 18.75: What carbonyl compounds are required to prepare a compound with mol...
- 18.76: Ninhydrin reacts with an amino acid to form a purple-colored compou...
- 18.77: A carboxylic acid is formed when an a -haloketone reacts with hydro...
- 18.78: An a , b -unsaturated carbonyl compound can be prepared by a reacti...
- 18.79: a. What carboxylic acid would be formed if the malonic ester synthe...
- 18.80: A Cannizzaro reaction is the reaction of an aldehyde that has no a ...
- 18.81: Propose a reasonable mechanism for each of the following reactions:
- 18.82: The following reaction is known as the benzoin condensation. The re...
- 18.83: Orsellinic acid, a common constituent of lichens, is synthesized fr...
- 18.84: Propose a mechanism for the following reaction. ( Hint: The interme...
- 18.85: A compound known as Hagemanns ester can be prepared by treating a m...
- 18.86: Amobarbital is a sedative marketed under the trade name Amytal. Pro...
- 18.87: Propose a reasonable mechanism for the following reaction:
Solutions for Chapter 18: Reactions at the A- Carbon of Carbonyl Compounds
Full solutions for Organic Chemistry | 7th Edition
ISBN: 9781269406772
Summary of Chapter 18: Reactions at the A- Carbon of Carbonyl Compounds
Many carbonyl compounds have a second site of reactivity—namely, a hydrogen bonded to a carbon that is adjacent to the carbonyl carbon. This hydrogen is sufficiently acidic to be removed by a strong base. The carbon adjacent to a carbonyl carbon is called an A -carbon so a hydrogen bonded to an a -carbon is called an A -hydrogen.
Organic Chemistry was written by and is associated to the ISBN: 9781269406772. Since 127 problems in chapter 18: Reactions at the A- Carbon of Carbonyl Compounds have been answered, more than 497985 students have viewed full step-by-step solutions from this chapter. Chapter 18: Reactions at the A- Carbon of Carbonyl Compounds includes 127 full step-by-step solutions. This expansive textbook survival guide covers the following chapters and their solutions. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 7.
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absolute temperature scale.
A temperature scale that uses the absolute zero of temperature as the lowest temperature. (5.3)
-
activated complex (transition state)
The particular arrangement of atoms found at the top of the potential-energy barrier as a reaction proceeds from reactants to products. (Section 14.5)
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alkene
A compound that possesses a carbon-carbon double bond.
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auxochrome
When applying Woodward-Fieser rules, the groups attached to the chromophore.
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Avogadro’s number (NA)
The number of 12C atoms in exactly 12 g of 12C; it equals 6.022 * 1023 mol-1. (Section 3.4)
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Chiral center
A tetrahedral atom, most commonly carbon, that is bonded to four different groups; also called a chirality center
-
chromatogram
In gas chromatography, a plot that identifies the retention time of each compound in the mixture.
-
dihydroxylation
A reaction characterized by the addition of two hydroxyl groups (OH) across an alkene.
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endothermic process
A process in which a system absorbs heat from its surroundings. (Section 5.2)
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Ground-state electron confi guration
The lowest-energy electron confi guration for an atom or molecule.
-
heterogeneous catalyst
A catalyst that does not dissolve in the reaction medium.
-
Imine
A compound containing a carbon-nitrogen double bond, R2C"NR’; also called a Schiff base
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matter waves
The term used to describe the wave characteristics of a moving particle. (Section 6.4)
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N terminus
For a peptide chain,the end that contains the amino group.
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organic chemistry
The study of carbon-containing compounds, typically containing carbon–carbon bonds. (Section 2.9; Chapter 24:Introduction)
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reductive amination
The conversion of a ketone or aldehyde into an imine under conditions in which the imine is reduced as soon as it is formed, giving an amine.
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spontaneous
A reaction with a negative DG, which means that products are favored at equilibrium.
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steric number
The total of (single bonds + lone pairs) for an atom in a compound.
-
Wittig reaction
A reaction that converts an aldehyde or ketone into an alkene, with the introduction of one or more carbon atoms.
-
Wolff-Kishner reduction
Reduction of the C"O group of an aldehyde or ketone to a CH2 group using hydrazine and a base. Ylide (Section 16.6)