EBK ESSENTIAL ORGANIC CHEMISTRY
EBK ESSENTIAL ORGANIC CHEMISTRY
3rd Edition
ISBN: 8220100659461
Author: Bruice
Publisher: PEARSON
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Chapter 13, Problem 51P

(a)

Interpretation Introduction

Interpretation:

Mechanism of compound are synthesized by the use of only provided carbon-containing compounds has to be given.

Concept introduction:

Required compounds are synthesized by the use of only provided carbon-containing compounds through a series of steps.

In first case, given alcohol is oxidized to a ketone. A strong base is added to the ketone. Aldol condensation reaction takes place. The aldol product is reduced and the final compound is obtained.

In second case, given alcohol is oxidized to a ketone. A strong base is added to the ketone. Aldol condensation reaction takes place. Hydrazine in alcoholic potassium hydroxide is added in the aldol condensation product to remove the carbonyl group. The intermediate alkene is reduced to give the final compound.

In third case, ethanol is oxidized to acetaldehyde. Acetaldehyde undergoes aldol addition reaction in presence of a strong base. Aldol addition product is reduced to form a diol compound 1. Other alcohol is oxidized to an acetone and converted to diol compound 2. Compound 1 and 2 combine to form the final product and two molecules of water are reduced.

(b)

Interpretation Introduction

Interpretation:

Mechanism of compound are synthesized by the use of only provided carbon-containing compounds has to be given.

Concept introduction:

Required compounds are synthesized by the use of only provided carbon-containing compounds through a series of steps.

In first case, given alcohol is oxidized to a ketone.  A strong base is added to the ketone. Aldol condensation reaction takes place. The aldol product is reduced and the final compound is obtained.

In second case, given alcohol is oxidized to a ketone. A strong base is added to the ketone

Aldol condensation reaction takes place. Hydrazine in alcoholic potassium hydroxide is added in the aldol condensation product to remove the carbonyl group. The intermediate alkene is reduced to give the final compound.

In third case, ethanol is oxidized to acetaldehyde.  Acetaldehyde undergoes aldol addition reaction in presence of a strong base. Aldol addition product is reduced to form a diol compound 1. Other alcohol is oxidized to an acetone and converted to diol compound 2. Compound 1 and 2 combine to form the final product and two molecules of water are reduced.

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For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. ? NH2 MgBr Will the first product that forms in this reaction create a new CC bond? ○ Yes ○ No MgBr ? Will the first product that forms in this reaction create a new CC bond? O Yes O No Click and drag to start drawing a structure. :☐ G x c olo Ar HE
Predicting As the lead product manager at OrganometALEKS Industries, you are trying to decide if the following reaction will make a molecule with a new C - C bond as its major product: H₂N O H 1. ? 2. H3O+ If this reaction will work, draw the major organic product or products you would expect in the drawing area below. If there's more than one major product, you can draw them in any arrangement you like. Be sure you use wedge and dash bonds if necessary, for example to distinguish between major products with different stereochemistry. 0 If the major products of this reaction won't have a new CC bond, just check the box under the drawing area and leave it blank. فا Explanation Check Click and drag to start drawing a structure.
Highlight the chirality (or stereogenic) center(s) in the given compound. A compound may have one or more stereogenic centers. OH OH OH OH OH OH
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How to Design a Total Synthesis; Author: Chemistry Unleashed;https://www.youtube.com/watch?v=9jRfAJJO7mM;License: Standard YouTube License, CC-BY