Textbook Question
What is the product of each of the following reactions?
a.
1429
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Ch. 11 - Organometallic Compounds
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
Chapter 12, Problem 15
What hydrocarbon would you use to prepare the organoboron compound in Problem 14?
Verified step by step guidance1
Analyze the structure of the organoboron compound provided in the image. The compound contains a boron atom bonded to two oxygen atoms in a cyclic structure (a catechol group) and a hydrocarbon chain attached to the boron atom.
Identify the hydrocarbon chain attached to the boron atom. In this case, the chain is a straight alkyl chain with five carbon atoms and a double bond between the second and third carbons, indicating it is 1-pentene.
Recall the hydroboration reaction mechanism, which involves the addition of borane (BH3) or a boron-containing reagent to an alkene. The boron atom adds to the less substituted carbon of the double bond, following anti-Markovnikov regioselectivity.
Determine the hydrocarbon needed for the reaction. Since the organoboron compound has a pentyl group with a double bond, the starting hydrocarbon should be 1-pentene, which will react with a boron reagent such as catecholborane.
Conclude that the hydrocarbon required to prepare the organoboron compound is 1-pentene, which undergoes hydroboration with catecholborane to yield the desired product.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Hydrocarbons
Hydrocarbons are organic compounds consisting entirely of hydrogen and carbon atoms. They serve as the fundamental building blocks for many organic reactions, including those involving organoboron compounds. Understanding the structure and reactivity of different types of hydrocarbons, such as alkanes, alkenes, and alkynes, is crucial for selecting the appropriate substrate for synthesis.
Recommended video:
Guided course
04:52
Aromaticity of Hydrocarbons
Organoboron Compounds
Organoboron compounds are organic molecules that contain boron atoms bonded to carbon. They are important intermediates in organic synthesis, particularly in cross-coupling reactions like the Suzuki reaction. Knowledge of how to prepare and utilize these compounds is essential for solving problems related to organic synthesis and reactivity.
Recommended video:
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01:40Defining meso compounds.
Synthesis Strategies
Synthesis strategies in organic chemistry involve the methods and pathways used to create specific compounds from simpler starting materials. This includes understanding functional group transformations, reactivity patterns, and the selection of appropriate reagents. A solid grasp of these strategies is necessary to determine which hydrocarbon can effectively yield the desired organoboron compound.
Recommended video:
1:16Synthesis of Amino Acids: Strecker Synthesis Example 1
Related Practice
Textbook Question
What is the product of each of the following reactions?
a.
1285
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Textbook Question
What aryl or vinylic halides would you use to synthesize the following compounds, using the alkenylorganoboron compound shown here?
c.
1397
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Textbook Question
What is the product of each of the following reactions?
b.
1078
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Textbook Question
The Stille reaction is similar to the Suzuki reaction. It replaces the alkenyl-organoboron compound of the Suzuki reaction with an alkenyl-organotin compound. (R is an alkyl group such as methyl or butyl.) Unlike the alkenyl-organoboron compound that always has a trans configuration, the alkenyl-organotin compound can have a cis configuration. What is the product of the Stille reaction shown here?
902
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Textbook Question
What is the product of each of the following reactions?
b.
921
views