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

Mullins 1st Edition

Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions

Problem 41a

Chapter 9, Problem 41a

Beginning with the molecules on the left of each chemical equation, synthesize the molecules shown. While there can be multiple ways of doing each synthesis, the minimum number of steps necessary is indicated over each reaction arrow.
(a)

Verified step by step guidance

Step 1: Perform a nucleophilic substitution reaction to replace the bromine atom with a hydroxyl group (-OH). This can be achieved using aqueous sodium hydroxide (NaOH) or another suitable nucleophile under appropriate conditions.

Step 2: Protect the hydroxyl group if necessary to prevent side reactions in subsequent steps. This can be done by converting the hydroxyl group into a protecting group, such as a silyl ether.

Step 3: Introduce the methyl group (-CH3) at the appropriate position using a methylating agent, such as methyl iodide (CH3I), in the presence of a base like potassium carbonate (K2CO3). Ensure regioselectivity to place the methyl group correctly.

Step 4: If a protecting group was used in Step 2, remove the protecting group to regenerate the hydroxyl group. This can be done using mild acidic or basic conditions, depending on the protecting group used.

Step 5: Verify the stereochemistry and functional group placement to ensure the final product matches the target molecule. Adjust reaction conditions if necessary to achieve the desired configuration.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above.

Video duration:

Was this helpful?

Key Concepts

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

Chemical Synthesis

Chemical synthesis refers to the process of creating complex chemical compounds from simpler ones through a series of chemical reactions. Understanding the principles of synthesis is crucial for determining the most efficient pathway to produce a desired molecule, often involving the selection of appropriate reagents and reaction conditions.

Reaction Mechanisms

A reaction mechanism is a detailed description of the step-by-step process by which reactants are converted into products. It includes the identification of intermediates and transition states, which helps in predicting the outcome of reactions and understanding how to manipulate conditions to favor the formation of specific products.

Stoichiometry

Stoichiometry is the calculation of reactants and products in chemical reactions based on the conservation of mass. It is essential for determining the proportions of substances involved in a synthesis, ensuring that the correct amounts are used to achieve the desired yield while minimizing waste.

Recommended video:

Guided course

02:08

Organic molecules in your everyday life.

Related Practice

Textbook Question

For each of the following ketones/aldehydes, indicate whether it is possible to synthesize it from an alkyne as the only compound in good (> 50%) yield. If so, how would you do it?

(d)

928

views

Textbook Question

When doing synthesis, you will often find yourself repeating the same series of steps. To see this in action, synthesize the following aldehydes beginning with an organic molecule containing three carbons or fewer.

(b)

1009

views

Textbook Question

Beginning with the molecules on the left of each chemical equation, synthesize the molecules shown. While there can be multiple ways of doing each synthesis, the minimum number of steps necessary is indicated over each reaction arrow.

(c)

(b)

(d)