Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions

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

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Mullins 1st Edition

Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions

Problem 41c

Chapter 9, Problem 41c

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)

Verified step by step guidance

Step 1: Perform an elimination reaction on the starting molecule (cyclopentylmethyl bromide) to form an alkene. Use a strong base, such as potassium tert-butoxide, to remove the bromine atom and generate cyclopentylmethyl alkene (CH2=CH-cyclopentane).

Step 2: Carry out an ozonolysis reaction on the alkene formed in Step 1. Use ozone (O3) followed by a reducing agent like dimethyl sulfide (DMS) or zinc in acetic acid to cleave the double bond and form two products: formaldehyde (H2C=O) and cyclopentylacetaldehyde.

Step 3: Oxidize the aldehyde group in cyclopentylacetaldehyde to a ketone. Use a mild oxidizing agent such as PCC (pyridinium chlorochromate) or a stronger oxidizing agent like Jones reagent (CrO3/H2SO4) to convert the aldehyde to cyclopentylacetone.

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Key Concepts

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

Synthesis in Organic Chemistry

Synthesis in organic chemistry refers to the process of constructing complex organic molecules from simpler ones through a series of chemical reactions. Understanding the synthesis pathway is crucial, as it involves selecting appropriate reagents and conditions to achieve the desired product efficiently. Each step in the synthesis must be carefully planned to minimize the number of reactions while maximizing yield.

Reaction Mechanisms

A reaction mechanism describes the step-by-step sequence of elementary reactions by which overall chemical change occurs. It provides insight into how reactants transform into products, including the formation and breaking of bonds. Familiarity with common mechanisms, such as nucleophilic substitution or elimination, is essential for predicting the outcomes of synthetic routes.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups is vital for understanding reactivity and guiding synthesis, as different groups can dictate the types of reactions that can occur. For example, carbonyl groups (C=O) are key in many synthesis pathways, including the formation of aldehydes and ketones.

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Related Practice

Textbook Question

Name the following alkynes according to the IUPAC rules of nomenclature.

(d)

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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.

(a)

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Textbook Question

Name the following alkynes according to the IUPAC rules of nomenclature.

(c)

(b)

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.

(d)

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Textbook Question

Name the following alkynes according to the IUPAC rules of nomenclature.

(b)

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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)

Verified video answer for a similar problem:

Key Concepts

Synthesis in Organic Chemistry

Reaction Mechanisms

Functional Groups

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)