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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 40d
Chapter 9, Problem 40d

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)

Verified step by step guidance
1
Step 1: Identify the target molecule, which is an aldehyde with a long carbon chain. The aldehyde group is characterized by a carbonyl group (C=O) bonded to a hydrogen atom.
Step 2: Begin with an organic molecule containing three carbons or fewer. A good starting point is ethanol (CH3CH2OH) or ethene (CH2=CH2), as these are simple and versatile precursors.
Step 3: Extend the carbon chain using reactions such as the Grignard reaction or alkylation. For example, you can use ethyl magnesium bromide (CH3CH2MgBr) to add carbon chains step by step.
Step 4: Introduce the aldehyde functional group by oxidizing a primary alcohol or selectively oxidizing a terminal alkene. For example, use PCC (pyridinium chlorochromate) to oxidize a primary alcohol to an aldehyde.
Step 5: Verify the structure of the synthesized molecule to ensure it matches the target aldehyde. Use spectroscopic techniques like IR (to confirm the presence of the C=O stretch) and NMR (to confirm the carbon chain and aldehyde group).

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Key Concepts

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

Aldehyde Synthesis

Aldehyde synthesis involves the formation of aldehyde functional groups, typically characterized by the presence of a carbonyl group (C=O) at the end of a carbon chain. Common methods for synthesizing aldehydes include oxidation of primary alcohols, hydrolysis of alkynes, and the use of specific reagents like DIBAL-H. Understanding these methods is crucial for effectively constructing aldehydes from simpler organic molecules.
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Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In organic chemistry, recognizing functional groups such as aldehydes, alcohols, and ketones is essential for predicting reactivity and guiding synthesis. The presence of a functional group often dictates the types of reactions a compound can undergo.
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Reaction Mechanisms

Reaction mechanisms describe the step-by-step process by which reactants are converted into products in a chemical reaction. Understanding these mechanisms is vital for predicting the outcomes of synthetic pathways, especially when multiple steps are involved. Knowledge of intermediates, transition states, and the role of catalysts can significantly aid in the synthesis of complex organic molecules.
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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?

(a)

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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)

2
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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)

2
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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)

6
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)

1
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.

(b)

2
views