ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
4th Edition
ISBN: 9781119761105
Author: Klein
Publisher: WILEY
Question
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Chapter 12, Problem 34PP

(a)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

 (b)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

(c)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

 (d)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

(e)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

(f)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

(g)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

(h)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

(i)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

(j)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

(k)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

(l)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

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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.
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