Textbook Question
Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer.
(b)
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Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
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Mullins 1st EditionCh. 10 - Alkynes: Electrophilic Addition and Redox ReactionsProblem 49g
Mullins 1st EditionCh. 10 - Alkynes: Electrophilic Addition and Redox ReactionsProblem 49gChapter 9, Problem 49g
Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer.
(g) 
Verified step by step guidance1
Step 1: Analyze the target molecule. The molecule contains a total of 9 carbons, including a hydroxyl group (-OH) attached to a chiral center. The structure also includes a long alkyl chain and a methyl group attached to the chiral center. The synthesis must begin with organic molecules containing three carbons or fewer.
Step 2: Begin by synthesizing the alkyl chain. Use ethyl bromide (C2H5Br) and a Grignard reagent derived from methyl bromide (CH3Br) to extend the carbon chain. Perform successive Grignard reactions to build the chain up to the desired length of 7 carbons.
Step 3: Introduce the hydroxyl group at the chiral center. Use a carbonyl compound, such as a ketone, to create the chiral center. React the ketone with a Grignard reagent to form the alcohol group (-OH) at the chiral center. Ensure stereoselectivity during this step to achieve the correct configuration.
Step 4: Add the methyl group to the chiral center. Use a methyl Grignard reagent (CH3MgBr) to attach the methyl group to the carbon adjacent to the hydroxyl group. This step will complete the chiral center with the correct stereochemistry.
Step 5: Verify the stereochemistry and purity of the final product. Use techniques such as NMR spectroscopy and chiral chromatography to confirm the structure and stereochemistry of the synthesized molecule. Adjust reaction conditions if necessary to optimize yield and stereoselectivity.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Understanding functional groups is essential for predicting the reactivity and properties of organic compounds. Common functional groups include hydroxyl (-OH), carboxyl (-COOH), and amine (-NH2), which can significantly influence the synthesis pathways of larger molecules.
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Identifying Functional Groups
Reactions of Organic Molecules
Organic synthesis often involves various types of chemical reactions, such as substitution, addition, and elimination reactions. Each reaction type has specific mechanisms and conditions under which they occur. Familiarity with these reactions allows chemists to design synthetic routes to create complex molecules from simpler precursors, particularly when starting with small organic molecules.
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02:17Identifying organic molecules
Carbon Skeletons
The carbon skeleton refers to the arrangement of carbon atoms in an organic molecule, which can be linear, branched, or cyclic. Understanding how to manipulate carbon skeletons is crucial for synthesizing larger molecules from smaller ones. In this context, starting with three-carbon or fewer molecules means recognizing how to build and modify these structures to achieve the desired target molecules.
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02:12Carbonation of Grignard Reagents
Related Practice
Textbook Question
The addition of H―X to alkynes has been shown to occur predominately via anti addition:
Two chemists disagreed on whether or not anti addition would happen on terminal alkynes as well. Suggest an experiment through which you could resolve this dispute.
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Textbook Question
In Section 10.8.1, you learned that alkenes react more quickly with electrophiles than do the corresponding alkynes (kalkene/kalkyne > 1). Explain why there is a greater disparity in the alkene versus alkyne reactivity in the addition of HBr as compared to the addition of Br2 [The rate data are not real, but are meant to illustrate a real trend.]
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Textbook Question
Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer.
(e)
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Textbook Question
Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer.
(f)
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Textbook Question
Trans addition is heavily favored for the addition of Br₂ and Cl₂ to alkynes. With chlorination, however, more of the syn addition product is formed. Rationalize this fact in light of your answer to Assessments 10.50 and 10.51.
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