Accomplishment of each of the given transformations is to be shown. Concept introduction: Swern Oxidation converts primary and secondary alcohols into aldehydes and ketones , respectively. The catalyst used is DMSO (dimethyl sulfoxide), oxalyl chloride in triethylamine (organic base). Reduction of alkyl halides to hydrocarbons is achieved by treating alkyl halides with lithium aluminum hydride ( LiAlH 4 ) . Chromic acid oxidation: Oxidation of primary alcohols to aldehydes and use of hydronium (aqueous medium) to further oxidize the aldehydes to carboxylic acids is achieved by chromic acid and water. Secondary alcohols are oxidized into ketones and no further reaction is involved, since there are no hydrogens attached to the oxygen to be removed. Pyridinium Chlorochromate (PPC): PPC is formed from pyridine, hydrochloric acid and chromium oxide. This allows for controlled oxidation since this reaction takes place in anhydrous conditions. Potassium Permanganate: Potassium permanganate is a strong oxidizing agent. It converts the primary alcohols and aldehydes to their corresponding carboxylic acids. It converts secondary alcohols to ketones. This is not a controlled reaction since the reaction occurs in aqueous medium. When an oxidation takes place, the hydrogen atom attached to the oxygen atom is removed to form aldehydes from alcohols, or to form carboxylic acids from aldehydes. Compounds with no hydrogen attached to oxygen cannot be oxidized using Swern oxidation. Examples of such compounds are tertiary alcohols and ethers.

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Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 12, Problem 5PP

Interpretation Introduction

Interpretation:

Accomplishment of each of the given transformations is to be shown.

Concept introduction:

Swern Oxidation converts primary and secondary alcohols into aldehydes and ketones, respectively. The catalyst used is DMSO (dimethyl sulfoxide), oxalyl chloride in triethylamine (organic base).

Reduction of alkyl halides to hydrocarbons is achieved by treating alkyl halides with lithium aluminum hydride (LiAlH4).

Chromic acid oxidation: Oxidation of primary alcohols to aldehydes and use of hydronium (aqueous medium) to further oxidize the aldehydes to carboxylic acids is achieved by chromic acid and water. Secondary alcohols are oxidized into ketones and no further reaction is involved, since there are no hydrogens attached to the oxygen to be removed.

Pyridinium Chlorochromate (PPC): PPC is formed from pyridine, hydrochloric acid and chromium oxide. This allows for controlled oxidation since this reaction takes place in anhydrous conditions.

Potassium Permanganate: Potassium permanganate is a strong oxidizing agent. It converts the primary alcohols and aldehydes to their corresponding carboxylic acids. It converts secondary alcohols to ketones. This is not a controlled reaction since the reaction occurs in aqueous medium.

When an oxidation takes place, the hydrogen atom attached to the oxygen atom is removed to form aldehydes from alcohols, or to form carboxylic acids from aldehydes. Compounds with no hydrogen attached to oxygen cannot be oxidized using Swern oxidation. Examples of such compounds are tertiary alcohols and ethers.

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Practice Problem 13.36b Problem 13.34 outlines a general method for the preparation of cis- or trans-disubstituted epoxides. Using that method, identify what reagents you would use to prepare the following epoxide from acetylene: H" 'Et The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A B C D DMP or PCC На, Pt EtBr PHCH2BR E F H H2SO4, H20, HgSO4 МСРВА (RCO3зН) Na, NH3 (/) H2, Lindlar's cat. I K TSCI, py PhBr NANH2 1) EtMgBr; 2) H30+

3) Propose suitable reagent(s) to accomplish the following transformations. (a) (b) Br N OH or

Propose suitable reagents to accomplish the following transformations.

Answer 2

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 12, Problem 5PP

Interpretation Introduction

Interpretation:

Accomplishment of each of the given transformations is to be shown.

Concept introduction:

Swern Oxidation converts primary and secondary alcohols into aldehydes and ketones, respectively. The catalyst used is DMSO (dimethyl sulfoxide), oxalyl chloride in triethylamine (organic base).

Reduction of alkyl halides to hydrocarbons is achieved by treating alkyl halides with lithium aluminum hydride (LiAlH4).

Chromic acid oxidation: Oxidation of primary alcohols to aldehydes and use of hydronium (aqueous medium) to further oxidize the aldehydes to carboxylic acids is achieved by chromic acid and water. Secondary alcohols are oxidized into ketones and no further reaction is involved, since there are no hydrogens attached to the oxygen to be removed.

Pyridinium Chlorochromate (PPC): PPC is formed from pyridine, hydrochloric acid and chromium oxide. This allows for controlled oxidation since this reaction takes place in anhydrous conditions.

Potassium Permanganate: Potassium permanganate is a strong oxidizing agent. It converts the primary alcohols and aldehydes to their corresponding carboxylic acids. It converts secondary alcohols to ketones. This is not a controlled reaction since the reaction occurs in aqueous medium.

When an oxidation takes place, the hydrogen atom attached to the oxygen atom is removed to form aldehydes from alcohols, or to form carboxylic acids from aldehydes. Compounds with no hydrogen attached to oxygen cannot be oxidized using Swern oxidation. Examples of such compounds are tertiary alcohols and ethers.

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Answer 3

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 12, Problem 5PP

Interpretation Introduction

Interpretation:

Accomplishment of each of the given transformations is to be shown.

Concept introduction:

Swern Oxidation converts primary and secondary alcohols into aldehydes and ketones, respectively. The catalyst used is DMSO (dimethyl sulfoxide), oxalyl chloride in triethylamine (organic base).

Reduction of alkyl halides to hydrocarbons is achieved by treating alkyl halides with lithium aluminum hydride (LiAlH4).

Chromic acid oxidation: Oxidation of primary alcohols to aldehydes and use of hydronium (aqueous medium) to further oxidize the aldehydes to carboxylic acids is achieved by chromic acid and water. Secondary alcohols are oxidized into ketones and no further reaction is involved, since there are no hydrogens attached to the oxygen to be removed.

Pyridinium Chlorochromate (PPC): PPC is formed from pyridine, hydrochloric acid and chromium oxide. This allows for controlled oxidation since this reaction takes place in anhydrous conditions.

Potassium Permanganate: Potassium permanganate is a strong oxidizing agent. It converts the primary alcohols and aldehydes to their corresponding carboxylic acids. It converts secondary alcohols to ketones. This is not a controlled reaction since the reaction occurs in aqueous medium.

When an oxidation takes place, the hydrogen atom attached to the oxygen atom is removed to form aldehydes from alcohols, or to form carboxylic acids from aldehydes. Compounds with no hydrogen attached to oxygen cannot be oxidized using Swern oxidation. Examples of such compounds are tertiary alcohols and ethers.

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Answer 4

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 12, Problem 5PP

Interpretation Introduction