Textbook Question
Beginning with an amide, two different pathways produce the same compound. Predict the product of these two pathways.
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Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
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Mullins 1st EditionCh. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid DerivativesProblem 59a
Mullins 1st EditionCh. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid DerivativesProblem 59aChapter 18, Problem 59a
Predict the product of the following reaction sequences.
(a) 
Verified step by step guidance1
Identify the starting material as a brominated alkane with a phenyl group attached, specifically (R)-1-phenylethyl bromide.
In the first step, sodium cyanide (NaCN) in tetrahydrofuran (THF) is used. This is a nucleophilic substitution reaction where the cyanide ion (CN-) will replace the bromine atom, forming a nitrile group. The product will be (R)-1-phenylethyl cyanide.
In the second step, lithium aluminum hydride (LiAlH4) in THF is used. LiAlH4 is a strong reducing agent that will reduce the nitrile group to a primary amine. The product will be (R)-1-phenylethylamine.
In the third step, the reaction mixture is quenched with H3O+. This step is typically used to neutralize any remaining reactive species and to protonate the amine, if necessary, to ensure the final product is in its neutral form.
The final product of the reaction sequence is (R)-1-phenylethylamine, which retains the stereochemistry of the starting material due to the nature of the reactions involved.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Reaction Mechanisms
Understanding reaction mechanisms is crucial in organic chemistry as they describe the step-by-step process by which reactants transform into products. This includes identifying intermediates, transition states, and the movement of electrons. A clear grasp of mechanisms helps predict the outcome of reactions and the stability of products formed.
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Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups allows chemists to predict reactivity and the types of reactions that can occur. For example, alcohols, carboxylic acids, and amines each have distinct behaviors in chemical reactions.
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Stereochemistry
Stereochemistry involves the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. It is essential for predicting the products of reactions, especially in cases where chirality or geometric isomerism plays a role. Understanding stereochemistry helps in determining the specific isomers that may be produced in a reaction.
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Related Practice
Textbook Question
Give the nitrile and organometallic reagent you would use to make the following ketones. There are two possible answers for both.
(b)
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Textbook Question
On a day in which the laboratory air conditioning stopped working, a chemist hypothesized that the atmosphere would provide enough ambient heat to drive the nitrile hydrolysis reaction to the carboxylic acid. Based on the IR of the resulting product, was this hypothesis correct?
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Textbook Question
Reduction of two different carboxylic acid derivatives with LiAlH₄ would give the amine shown. Identify these carboxylic acid derivatives.
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Textbook Question
Give the nitrile and organometallic reagent you would use to make the following ketones. There are two possible answers for both.
(a)
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Textbook Question
Predict the product of the following reaction sequences.
(b)
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