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Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
All textbooksMullins 1st EditionCh. 10 - Alkynes: Electrophilic Addition and Redox ReactionsProblem 49e
Chapter 9, Problem 49e

Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer.
(e) Chemical structure showing a carbon chain with hydroxyl (OH) and chlorine (Cl) functional groups attached.

Verified step by step guidance
1
Step 1: Analyze the target molecule and identify its functional groups, carbon skeleton, and any stereochemistry. Determine the number of carbons in the molecule and compare it to the starting materials (organic molecules with three carbons or fewer).
Step 2: Break down the synthesis into smaller steps by identifying key transformations required to build the target molecule. Consider reactions such as chain elongation, functional group interconversion, and stereochemical control.
Step 3: Select appropriate starting materials (e.g., propane, propene, propyne, or other three-carbon molecules) and determine how to modify them to introduce the necessary functional groups or extend the carbon chain. Use reactions like alkylation, oxidation, or addition reactions.
Step 4: Plan the sequence of reactions to achieve the desired connectivity and functional groups. For example, if chain elongation is required, use reactions like the Grignard reaction, aldol condensation, or Wittig reaction. If functional group interconversion is needed, consider reactions like reduction, oxidation, or substitution.
Step 5: Verify the feasibility of each step by considering reaction conditions, regioselectivity, and stereoselectivity. Ensure that the synthesis is efficient and avoids unnecessary steps or side reactions.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Alkane Structure and Reactivity

Alkanes are saturated hydrocarbons consisting only of carbon and hydrogen atoms, with single bonds between carbon atoms. Understanding their structure is crucial for synthesis, as they serve as the simplest organic molecules. The reactivity of alkanes is limited compared to other functional groups, but they can undergo reactions such as combustion and halogenation, which are foundational in organic synthesis.
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Functional Groups

Functional groups are specific groups of atoms within molecules that determine the chemical reactivity and properties of those molecules. In organic chemistry, common functional groups include alcohols, aldehydes, and carboxylic acids. Recognizing and manipulating these groups is essential for synthesizing more complex molecules from simpler precursors, especially when starting with three-carbon or smaller organic molecules.
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Synthetic Pathways

Synthetic pathways refer to the series of chemical reactions that transform starting materials into desired products. In organic synthesis, understanding how to navigate these pathways is vital for constructing complex molecules from simpler ones. This involves knowledge of reaction mechanisms, conditions, and the ability to predict the outcomes of reactions, which is particularly important when working with limited starting materials like those containing three carbons or fewer.
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Related Practice
Textbook Question

Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer.

(b)

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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

Beginning with the molecules on the left, provide a synthesis of the molecule on the right. The ideal number of steps is indicated over the reaction arrow, although there may be alternate routes worth considering.

(b)

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Textbook Question

Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer.

(g)

Textbook Question

Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer.

(f)

1
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Textbook Question

Beginning with the molecules on the left, provide a synthesis of the molecule on the right. The ideal number of steps is indicated over the reaction arrow, although there may be alternate routes worth considering.

(a)

2
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