Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination

Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition

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Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination

Problem 104c

Chapter 12, Problem 104c

Suggest a synthesis for the following molecules beginning with organic molecules containing three or fewer carbons. [You will need to use a protecting group in these syntheses.]
(c)

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Identify the target molecule and determine the functional groups present. Consider the carbon skeleton and any functional groups that need to be introduced or transformed.

Select a suitable starting material with three or fewer carbons that can be transformed into the target molecule. Consider the functional groups and carbon framework needed.

Plan the synthesis by identifying key transformations. Consider the use of protecting groups to temporarily mask reactive functional groups during the synthesis.

Determine the sequence of reactions needed to convert the starting material into the target molecule. Include steps for introducing or modifying functional groups, and for adding carbon atoms if necessary.

Consider the use of reagents and conditions for each step, ensuring compatibility with the protecting groups used. Plan for the deprotection step to reveal the desired functional group in the final product.

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Key Concepts

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

Synthesis Strategy

A synthesis strategy involves planning a sequence of chemical reactions to construct a target molecule from simpler starting materials. It requires understanding reaction mechanisms, functional group transformations, and the order of steps to efficiently build complex structures while minimizing side reactions.

Protecting Groups

Protecting groups are chemical groups temporarily added to a molecule to shield reactive sites during a synthesis. They prevent unwanted reactions at specific functional groups, allowing selective transformations elsewhere in the molecule. After the desired reactions are complete, protecting groups are removed to reveal the original functionality.

Functional Group Interconversion

Functional group interconversion involves transforming one functional group into another to achieve the desired chemical structure. This concept is crucial in organic synthesis, enabling chemists to modify molecules by converting alcohols to ketones, alkenes to alcohols, or other transformations necessary for constructing complex molecules.

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Textbook Question

The reaction of alkoxides with haloalkanes is not a viable way to form ethers. (a) Why? (b) Why can thioethers be formed by an analogous reaction?

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Textbook Question

Suggest a synthesis for the following molecules beginning with organic molecules containing three or fewer carbons. [You will need to use a protecting group in these syntheses.]

(a)

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Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (iv) 1. TsCl, Et₃N 2. NaCN ; (v) 1. TsCl, Et₃N 2. NaOt-Bu . If no reaction occurs, write 'no reaction.'

(a)

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Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (vi) H₂SO₄. If no reaction occurs, write 'no reaction.'

(a)

Textbook Question

In contrast to Assessment 13.102, only one combination of haloalkane and alkoxide can be used in the Williamson ether synthesis to make the ether shown. Identify the combination and explain why it is the only combination that works.

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Textbook Question

Suggest a synthesis for the following molecules beginning with organic molecules containing three or fewer carbons. [You will need to use a protecting group in these syntheses.]

(b)

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Suggest a synthesis for the following molecules beginning with organic molecules containing three or fewer carbons. [You will need to use a protecting group in these syntheses.] (c)

Verified video answer for a similar problem:

Key Concepts

Synthesis Strategy

Protecting Groups

Functional Group Interconversion

Suggest a synthesis for the following molecules beginning with organic molecules containing three or fewer carbons. [You will need to use a protecting group in these syntheses.]
(c)