Textbook Question
Show how this 1° alcohol can be made from the following:
(c) a 7-carbon aldehyde
(d) a carboxylic acid
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Ch.10 - Structure and Synthesis of Alcohols
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 10, Problem 57e,f
Show how this 1° alcohol can be made from the following:
(e) an alkene
(f) ethylene oxide
Verified step by step guidance1
Step 1: To synthesize the given 1° alcohol from an alkene, identify the corresponding alkene structure. The alcohol shown has a hydroxyl group (-OH) attached to a primary carbon. The alkene precursor would be cyclopentyl ethene (cyclopentyl group attached to a double bond).
Step 2: Perform hydroboration-oxidation on the alkene. This reaction involves two steps: (a) Add BH₃ (borane) or a borane derivative to the alkene to form an organoborane intermediate. (b) Oxidize the organoborane intermediate using H₂O₂ (hydrogen peroxide) in a basic solution (NaOH). This results in anti-Markovnikov addition of water, forming the 1° alcohol.
Step 3: To synthesize the given 1° alcohol from ethylene oxide, identify the nucleophile that can attack the ethylene oxide ring. The nucleophile in this case would be cyclopentylmethyl anion (generated from cyclopentylmethyl bromide using a strong base like NaH).
Step 4: Perform a ring-opening reaction of ethylene oxide. The nucleophile attacks the less hindered carbon of the ethylene oxide ring, leading to the formation of a primary alcohol. This reaction is typically carried out in an aqueous or alcohol solvent.
Step 5: After the ring-opening reaction, ensure the product matches the structure of the desired 1° alcohol. Verify that the hydroxyl group is attached to the primary carbon and the cyclopentyl group is intact.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Alcohol Synthesis from Alkenes
The conversion of alkenes to alcohols typically involves hydration reactions. This can be achieved through acid-catalyzed hydration, where water adds across the double bond of the alkene, or through hydroboration-oxidation, which provides anti-Markovnikov addition. Understanding the mechanism and regioselectivity of these reactions is crucial for synthesizing the desired primary alcohol.
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Forming alcohols through SN2 reactions.
Ethylene Oxide as a Reactant
Ethylene oxide is a cyclic ether that can be used to produce alcohols through ring-opening reactions. When reacted with nucleophiles, such as alcohols or water, the strained ring opens, leading to the formation of a primary alcohol. This reaction is significant in organic synthesis, particularly for creating alcohols with specific stereochemistry.
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Regioselectivity in Organic Reactions
Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In the context of alcohol synthesis, understanding regioselectivity is essential to predict the major product formed from alkenes or cyclic ethers, ensuring the correct primary alcohol is synthesized based on the reaction conditions and reagents used.
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Related Practice
Textbook Question
For each synthesis, start with bromocyclohexane and predict the products. Assume that an excess of each reactant is added so that all possible reactions that can happen will happen.
(c)
899
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Textbook Question
For each synthesis, start with bromocyclohexane and predict the products. Assume that an excess of each reactant is added so that all possible reactions that can happen will happen.
(a)
1630
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Textbook Question
For each synthesis, start with bromocyclohexane and predict the products. Assume that an excess of each reactant is added so that all possible reactions that can happen will happen.
(b)
698
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Textbook Question
Show how this 1° alcohol can be made from the following:
(a) a 1° alkyl bromide
827
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Textbook Question
Show how this 1° alcohol can be made from the following:
(b) formaldehyde
1217
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