Textbook Question
Excess ammonia must be used when a primary amine is synthesized by reductive amination. What product will be obtained if the reaction is carried out with excess carbonyl compound?
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Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblem 31
Bruice 8th EditionCh. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid DerivativesProblem 31Chapter 17, Problem 31
Imines can exist as stereoisomers. The isomers are named using the E,Z system of nomenclature (Section 4.2 ). The lone pair has the lowest priority.
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Draw the structure of each of the following compounds:
a. the (E)-hydrazone of benzaldehyde
b. the (Z)-oxime of propiophenone
Verified step by step guidance1
Step 1: Understand the E,Z nomenclature system. In this system, the priority of substituents around a double bond is determined using the Cahn-Ingold-Prelog rules. The (E)-isomer has the higher priority groups on opposite sides of the double bond, while the (Z)-isomer has them on the same side.
Step 2: For part (a), the (E)-hydrazone of benzaldehyde, start by identifying the structure of benzaldehyde (C6H5CHO). Replace the oxygen in the aldehyde group with a hydrazone group (-NH-NH2). Then, arrange the substituents such that the higher priority groups (phenyl group and hydrazone group) are on opposite sides of the C=N double bond.
Step 3: For part (b), the (Z)-oxime of propiophenone, begin by identifying the structure of propiophenone (C6H5-CO-CH3). Replace the oxygen in the ketone group with an oxime group (-C=N-OH). Arrange the substituents such that the higher priority groups (phenyl group and oxime group) are on the same side of the C=N double bond.
Step 4: Use the lone pair on the nitrogen atom to determine the lowest priority group in both cases. Ensure that the lone pair is correctly positioned according to the E,Z configuration rules.
Step 5: Draw the final structures for both compounds, ensuring that the stereochemistry matches the (E) and (Z) configurations as described. Verify the placement of substituents and lone pairs to confirm the correct stereoisomer.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
E/Z Nomenclature
The E/Z system is a method for describing the stereochemistry of alkenes and imines based on the Cahn-Ingold-Prelog priority rules. In this system, 'E' (from the German 'entgegen') indicates that the highest priority substituents on either side of a double bond are on opposite sides, while 'Z' (from 'zusammen') indicates they are on the same side. This nomenclature is crucial for distinguishing between different stereoisomers.
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E/Z Diastereoisomerism
Imines
Imines are organic compounds characterized by a carbon-nitrogen double bond (C=N), where the nitrogen atom is typically bonded to a hydrogen atom or an organic group. They are formed through the condensation of an amine and a carbonyl compound, such as an aldehyde or ketone. Imines can exhibit stereoisomerism due to the presence of the double bond, allowing for E/Z configurations.
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Hydrazones and Oximes
Hydrazones and oximes are specific types of imines formed from hydrazines and hydroxylamines, respectively. A hydrazone is formed when a hydrazine reacts with a carbonyl compound, while an oxime is produced when a hydroxylamine reacts with a carbonyl compound. Both types of compounds can also exhibit E/Z stereoisomerism, depending on the arrangement of substituents around the C=N bond.
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Related Practice
Textbook Question
What are the products of the following reactions? (A trace amount of acid is present in each case.)
a. cyclopentanone + ethylamine
b. cyclopentanone + diethylamine
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Textbook Question
The compounds commonly known as 'amino acids' are actually α-aminocarboxylic-aminocarboxylic acids. What carbonyl compounds should be used to synthesize the two amino acids shown here?
a.
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Textbook Question
Why is the pKa value of protonated hydroxylamine (6.0) so much lower than the value of a protonated primary amine such as protonated methylamine (10.7)?
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Textbook Question
A ketone can be prepared from the reaction of a nitrile with a Grignard reagent. Describe the intermediate formed in this reaction, and show how it can be converted to a ketone.
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Textbook Question
The pKa of protonated acetone is about –7.5 and the pKa of protonated hydroxylamine is 6.0.
a. In a reaction with hydroxylamine at pH 4.5 (Figure 16.2), what fraction of acetone is present in its acidic, protonated form?
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