Textbook Question
Show how you would synthesize each compound, starting with an ester containing no more than eight carbon atoms. Any other necessary reagents may be used.
(a) Ph3C–OH
(b) (PhCH2)2CHOH
(c) PhCONHCH2CH3
1
views
Ch. 21 - Carboxylic Acid Derivatives
Wade9th EditionOrganic ChemistryISBN: 9780135213728
Not the one you use?Change textbookSelect a different textbook
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 21, Problem 34c
Suggest the most appropriate reagent for each synthesis, and explain your choice.
(c) 
Verified step by step guidance1
Step 1: Analyze the transformation. The starting material is a ketone with a methoxy group (-OCH3) attached to the carbonyl carbon. The product is an alcohol (-CH2OH) where the methoxy group has been replaced by a hydroxymethyl group.
Step 2: Recognize the type of reaction. This transformation involves the reduction of the ester functional group (-COOCH3) to a primary alcohol (-CH2OH). This suggests the use of a reducing agent.
Step 3: Identify the appropriate reagent. Lithium aluminum hydride (LiAlH4) is a strong reducing agent commonly used to reduce esters to primary alcohols. It selectively reduces the ester group without affecting the double bond in the molecule.
Step 4: Explain the mechanism. LiAlH4 donates hydride ions (H-) to the carbonyl carbon of the ester, breaking the C=O bond and forming an intermediate alkoxide. Subsequent protonation during workup converts the alkoxide to the alcohol (-CH2OH).
Step 5: Note reaction conditions. The reaction typically requires an anhydrous solvent like ether and careful handling due to the reactivity of LiAlH4. After reduction, the reaction mixture is quenched with water or an acid to complete the conversion to the alcohol.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
2mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Reagents in Organic Synthesis
Reagents are substances used in chemical reactions to facilitate the transformation of reactants into products. In organic synthesis, the choice of reagent is crucial as it determines the reaction pathway, the functional groups involved, and the overall yield of the desired product. Understanding the properties and reactivity of various reagents is essential for selecting the most appropriate one for a specific synthesis.
Recommended video:
1:16
Synthesis of Amino Acids: Strecker Synthesis Example 1
Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Identifying the functional groups present in the starting materials and the desired product is vital for determining which reagents will effectively facilitate the necessary transformations. Knowledge of common functional groups helps predict reactivity and selectivity in organic reactions.
Recommended video:
Guided course
02:36Identifying Functional Groups
Reaction Mechanisms
A reaction mechanism is a step-by-step description of the process by which reactants are converted into products. Understanding the mechanism provides insight into how and why certain reagents are chosen, as it reveals the intermediates formed and the energy changes involved. This knowledge is essential for predicting the outcomes of reactions and for troubleshooting synthesis problems.
Recommended video:
Guided course
02:16Heck Reaction Mechanism
Related Practice
Textbook Question
Suggest the most appropriate reagent for each synthesis, and explain your choice.
(b)
2
views
Textbook Question
Show how you would synthesize each compound, starting with an ester containing no more than eight carbon atoms. Any other necessary reagents may be used.
(d) Ph2CHOH
(e) PhCH2OH
(f) PhCOOH
1
views
Textbook Question
Show how you would use anhydrides to synthesize the following compounds. In each case, explain why an anhydride might be preferable to an acid chloride.
(c) phthalic acid monoamide
(d) succinic acid monomethyl ester
2
views
Textbook Question
Suggest the most appropriate reagent for each synthesis, and explain your choice.
(d)
1
views
Textbook Question
Suggest the most appropriate reagent for each synthesis, and explain your choice.
(a)
1
views