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Ch. 7 - Structure and Synthesis of Alkenes; Elimination
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
Chapter 7, Problem 37a

For practice in recognizing mechanisms, classify each reaction according to the type of mechanism you expect:
1. Free-radical chain reaction
2. Reaction involving strong bases and strong nucleophiles
3. Reaction involving strong acids and strong electrophiles
(a)

Verified step by step guidance
1
Examine the reactants and products in the given reaction. The reactants are two molecules of acetone (CH₃COCH₃) and the reagent is barium hydroxide (Ba(OH)₂). The product is an aldol condensation product, which is a β-hydroxy ketone.
Recognize that the presence of Ba(OH)₂ suggests a reaction involving a strong base. Barium hydroxide is a strong base that can deprotonate the α-hydrogen of acetone, forming an enolate ion.
Understand the mechanism: The enolate ion formed from acetone acts as a nucleophile and attacks the carbonyl carbon of another acetone molecule, leading to the formation of a new carbon-carbon bond.
Identify the type of reaction: This is an aldol condensation reaction, which typically involves strong bases and nucleophiles. The enolate ion is a strong nucleophile, and the carbonyl carbon is an electrophile.
Classify the reaction: Based on the mechanism and the involvement of strong bases and nucleophiles, this reaction falls under category B: Reaction involving strong bases and strong nucleophiles.

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Key Concepts

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

Free-Radical Chain Reactions

Free-radical chain reactions involve a series of steps including initiation, propagation, and termination, where free radicals are generated and react with stable molecules. These reactions are characterized by the formation of new radicals that continue the reaction cycle. Common examples include the halogenation of alkanes, where a halogen radical abstracts a hydrogen atom, leading to a chain reaction.
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Nucleophiles and Electrophiles

Nucleophiles are species that donate an electron pair to form a chemical bond, while electrophiles are electron-deficient species that accept an electron pair. Strong bases often act as nucleophiles, attacking electrophilic centers in reactions. Understanding the roles of these species is crucial for predicting reaction mechanisms and outcomes in organic chemistry.
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Mechanisms of Organic Reactions

The mechanism of an organic reaction describes the step-by-step process by which reactants are converted into products, detailing the breaking and forming of bonds. Mechanisms can be classified based on the nature of the reactants and the conditions, such as whether they involve ionic or radical pathways. Recognizing these mechanisms helps in understanding reaction conditions and predicting product formation.
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Related Practice
Textbook Question

Show the product(s) you expect from dehydration of the following alcohols when they are heated in sulfuric or phosphoric acid. In each case, use a mechanism to show how the products are formed.

(b)

977
views
Textbook Question

Show the product(s) you expect from dehydration of the following alcohols when they are heated in sulfuric or phosphoric acid. In each case, use a mechanism to show how the products are formed.

(c)

697
views
Textbook Question

For practice in recognizing mechanisms, classify each reaction according to the type of mechanism you expect:

1. Free-radical chain reaction

2. Reaction involving strong bases and strong nucleophiles

3. Reaction involving strong acids and strong electrophiles

(b)

1518
views
Textbook Question

For practice in recognizing mechanisms, classify each reaction according to the type of mechanism you expect:

1. Free-radical chain reaction

2. Reaction involving strong bases and strong nucleophiles

3. Reaction involving strong acids and strong electrophiles

(c)

1526
views
Textbook Question

The dehydrogenation of butane to trans-but-2-ene has ΔH° = +116 kJ/mol (+27.6 kcal/mol) and ΔS° = +117J/kelvin-mol (+28.0 cal/kelvin-mol).

a. Compute the value of ΔG° for dehydrogenation at room temperature (25 °C or 298 °K). Is dehydrogenation favored or disfavored?

HINT: When you are doing synthesis problems, avoid using these high-temperature industrial methods. They require specialized equipment, and they produce variable mixtures of products.

1068
views
Textbook Question

For practice in recognizing mechanisms, classify each reaction according to the type of mechanism you expect:

1. Free-radical chain reaction

2. Reaction involving strong bases and strong nucleophiles

3. Reaction involving strong acids and strong electrophiles.

(d)

1435
views