Domanda del libro di testo
Draw the mechanism for formation of the two addition products.
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Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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TOC.tableOfContents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding31
- 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. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblema 36a
Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblema 36aCapitolo 10, Problema 36a
The existence of the NIH shift was established by determining the major product obtained from rearrangement of the following arene oxide, in which a hydrogen has been replaced by a deuterium.
a. What would be the major product if the NIH shift occurs? (Hint: A C—H bond is easier to break than a C—D bond.)
Guida verificata passo dopo passo1
Step 1: Analyze the structure of the arene oxide provided in the image. The molecule contains a deuterium (D) atom and a hydrogen (H) atom attached to the same carbon adjacent to the epoxide group. The epoxide group is highly reactive and prone to rearrangement under acidic conditions (HB⁺).
Step 2: Understand the NIH shift mechanism. The NIH shift involves the migration of a hydrogen (or deuterium) atom during the rearrangement of the arene oxide. This occurs due to the breaking of the C-H or C-D bond and subsequent reattachment to a neighboring carbon atom.
Step 3: Consider the bond strength of C-H versus C-D. The C-H bond is easier to break than the C-D bond because the C-D bond is stronger due to the heavier mass of deuterium. This means the hydrogen atom is more likely to migrate during the NIH shift.
Step 4: Predict the rearrangement product. During the NIH shift, the hydrogen atom (H) migrates to the neighboring carbon atom, while the deuterium (D) remains in its original position. This results in the formation of a rearranged product where the hydrogen is now attached to a different carbon.
Step 5: Verify the major product. The major product will have the hydrogen atom relocated to the neighboring carbon, while the deuterium remains unchanged. This rearrangement stabilizes the molecule and completes the NIH shift process.
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NIH Shift
The NIH shift refers to a specific rearrangement mechanism in organic chemistry where a hydrogen atom is replaced by a deuterium atom during the reaction. This shift is significant in understanding the behavior of arene oxides, as it illustrates how the stability of intermediates can influence the final product. The NIH shift is particularly relevant when considering the bond strengths of C—H versus C—D bonds, as the latter is generally stronger.
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03:43
Alkyl Shift
Arene Oxides
Arene oxides are reactive intermediates formed from the oxidation of aromatic compounds. They are characterized by an epoxide-like structure where an oxygen atom is bonded to a carbon atom in the aromatic ring. Understanding the reactivity of arene oxides is crucial for predicting the outcomes of various organic reactions, including rearrangements like the NIH shift, as they can lead to different products based on the stability of the resulting structures.
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03:20Benzylic Oxidation
Isotope Effects
Isotope effects refer to the differences in reaction rates or mechanisms that occur when isotopes of an element are substituted in a molecule. In this context, the presence of deuterium (D) instead of hydrogen (H) affects the bond strength, making C—D bonds stronger and less likely to break compared to C—H bonds. This concept is essential for predicting the major product of the NIH shift, as it influences which bond will break during the rearrangement process.
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03:06Understanding the hydrogen isotopes.
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The existence of the NIH shift was established by determining the major product obtained from rearrangement of the following arene oxide, in which a hydrogen has been replaced by a deuterium.
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