Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
bartleby

Concept explainers

bartleby

Videos

Question
Book Icon
Chapter 11, Problem 11.38P
Interpretation Introduction

(a)

Interpretation:

The detailed mechanism for the given reaction with major product is to be drawn.

Concept introduction:

Alkynes are electron rich system like alkenes and can undergo electrophilic addition of water in acidic condition to produce the enol form. This enol form, on acid catalyzed tautomerization, converts to a stable keto form, i.e., corresponding aldehyde or ketone. The acid in aqueous solution gets dissociated and forms hydronium ion H3O+. The reaction proceeds with proton transfer reaction to form a stable vinylic carbocation, followed by the action of water as a nucleophile. The deuterium is a isotope of hydrogen atom and reacts like hydrogen.

Interpretation Introduction

(b)

Interpretation:

The detailed mechanism for the given reaction with major product is to be drawn.

Concept introduction:

Alkynes are electron rich system like alkenes and can undergo electrophilic addition of water in acidic condition to produce the enol form. This enol form, on acid catalyzed tautomerization, converts to a stable keto form, i.e., corresponding aldehyde or ketone. The acid in aqueous solution gets dissociated and forms hydronium ion H3O+. The reaction proceeds with proton transfer reaction to form a stable vinylic carbocation, followed by the action of water as a nucleophile. The deuterium is a isotope of hydrogen atom and reacts like hydrogen.

Interpretation Introduction

(c)

Interpretation:

The detailed mechanism for the given reaction with major product is to be drawn.

Concept introduction:

Alkynes are electron rich system like alkenes and can undergo electrophilic addition of water in acidic condition to produce the enol form. This enol form, on acid catalyzed tautomerization, converts to a stable keto form, i.e., corresponding aldehyde or ketone. The acid in aqueous solution gets dissociated and forms hydronium ion H3O+. The reaction proceeds with proton transfer reaction to form a stable vinylic carbocation, followed by the action of water as a nucleophile. The deuterium is an isotope of hydrogen atom and reacts like hydrogen.

Blurred answer
Students have asked these similar questions
3:48 PM Fri Apr 4 K Problem 4 of 10 Submit Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. Mg. :0: Select to Add Arrows :0: :Br: Mg :0: :0: Select to Add Arrows Mg. Br: :0: 0:0- Br -190 H 0:0 Select to Add Arrows Select to Add Arrows neutralizing workup H CH3
I
Draw the Markovnikov product of the hydrobromination of this alkene. Note for advanced students: draw only one product, and don't worry about showing any stereochemistry. Drawing dash and wedge bonds has been disabled for this problem. + Explanation Check 1 X E 4 1 1 1 1 1 HBr Click and drag to start drawing a structure. 80 LE #3 @ 2 $4 0 I அ2 % 85 F * K M ? BH 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use Privacy Center & 6 27 FG F10 8 9 R T Y U D F G H P J K L Z X C V B N M Q W A S H option command H command opti

Chapter 11 Solutions

Organic Chemistry: Principles and Mechanisms (Second Edition)

Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
How to Design a Total Synthesis; Author: Chemistry Unleashed;https://www.youtube.com/watch?v=9jRfAJJO7mM;License: Standard YouTube License, CC-BY