Organic Chemistry - Standalone book
Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
Question
Book Icon
Chapter 9, Problem 34P
Interpretation Introduction

Interpretation:

Using acetylene and other necessary organic and inorganic reagents, the synthesis of 2heptanone is to be described.

Concept Introduction:

>

Alkylation of acetylene takes place in two steps. Acetylene has two acidic protons which can be abstracted by a strong base.

>

The acetylene is treated with sodium amide to convert the acetylene to its conjugate base in the second step.

>

The acetylide ion reacts with an alkyl halide in the first step forming a new carbon-carbon bond. The halide ion is displaced by SN2 type of reaction.

>

This sequence converts acetylene to its monosubstituted derivative which is also a terminal alkyne.

>

Repeating this sequence of steps using a different alkyl halide converts the acetylene to its disubstituted derivative. The triple bond is internal in this derivative.

>

Hydration of alkynes takes place in two steps producing ketone as the final product.

>

In the first step, addition of water to the triple bond takes place according to Markovnikov's rule. Hydrogen gets attached to the triple bonded carbon atom having more hydrogens attached to it.

>

This addition reaction produces an enol which changes to ketone by tautomerization.

>

The overall addition reactionemploys mercury (II) sulfate as a catalyst.

Blurred answer
Students have asked these similar questions
What would be the best choices for the missing reagents 1 and 3 in this synthesis? 1 1. PPh3 2. n-BuLi 2 • Draw the missing reagents in the drawing area below. You can draw them in any arrangement you like. • Do not draw the missing reagent 2. If you draw 1 correctly, we'll know what it is. • Note: if one of your reagents needs to contain a halogen, use bromine. Click and drag to start drawing a structure.
The product on the right-hand side of this reaction can be prepared from two organic reactants, under the conditions shown above and below the arrow. Draw 1 and 2 below, in any arrangement you like. 1+2 NaBH₂CN H+ N Click and drag to start drawing a structure. X $
Explain what is the maximum absorbance of in which caffeine absorbs?

Chapter 9 Solutions

Organic Chemistry - Standalone book

Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning
Text book image
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning