Textbook Question
Show how you would accomplish the following syntheses. You may use whatever additional reagents you need.
(e)
1
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Ch. 18 - Ketones and Aldehydes
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 18, Problem 29f
Show how you would accomplish the following syntheses. You may use whatever additional reagents you need.
(f) 
Verified step by step guidance1
Step 1: Identify the functional group transformation. The starting material contains a bromine atom attached to a carbon chain, and the product contains a terminal alkyne (-C≡CH). This suggests that the bromine atom will be replaced by an alkyne group through an elimination reaction followed by alkyne formation.
Step 2: Perform an elimination reaction to remove the bromine atom and form an alkene. Use a strong base such as potassium tert-butoxide (KOtBu) or sodium amide (NaNH2) to deprotonate the β-hydrogen and eliminate HBr, forming a double bond (alkene).
Step 3: Convert the alkene to a terminal alkyne. Treat the alkene with a strong base like sodium amide (NaNH2) in liquid ammonia (NH3) to generate the acetylide ion, followed by protonation with water or an acid to form the terminal alkyne.
Step 4: Ensure the carbonyl group (C=O) remains intact during the reaction. The reagents used for elimination and alkyne formation should not interfere with the ketone functional group.
Step 5: Verify the structure of the product. The final product should have the terminal alkyne (-C≡CH) attached to the carbon chain, with the ketone group (C=O) preserved at the original position.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Organic Synthesis
Organic synthesis is the process of constructing organic compounds through chemical reactions. It involves the strategic selection of starting materials and reagents to achieve desired products. Understanding the principles of synthesis is crucial for designing pathways that efficiently convert reactants into target molecules while considering factors like yield and selectivity.
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Reagents and Reaction Mechanisms
Reagents are substances used in chemical reactions to facilitate the transformation of reactants into products. Each reagent can influence the reaction mechanism, which describes the step-by-step process of how reactants are converted into products. Familiarity with common reagents and their mechanisms is essential for predicting the outcomes of synthetic routes.
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Functional Groups
Functional groups are specific groups of atoms within molecules that determine the chemical properties and reactivity of those molecules. Recognizing functional groups is vital in organic chemistry, as they guide the selection of appropriate reactions and reagents for synthesis. Understanding how different functional groups interact can help in predicting the behavior of compounds during chemical transformations.
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Related Practice
Textbook Question
Show how you would accomplish the following syntheses. You may use whatever additional reagents you need.
(d)
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Textbook Question
Trimethylphosphine is a stronger nucleophile than triphenylphosphine, but it is rarely used to make ylides. Why is trimethylphosphine unsuitable for making most phosphorus ylides?
1
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Textbook Question
Show how you would accomplish the following syntheses. You may use whatever additional reagents you need.
(c)
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Textbook Question
Like other strong nucleophiles, triphenylphosphine attacks and opens epoxides. The initial product (a betaine) quickly cyclizes to an oxaphosphetane that collapses to an alkene and triphenylphosphine oxide.
(a) Show each step in the reaction of trans-2,3-epoxybutane with triphenylphosphine to give but-2-ene. What is the stereochemistry of the double bond in the product?
9
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Textbook Question
Write the sequence of steps required for the conversion of benzene into benzenediazonium chloride.
1
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