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explnation of the mechanism step by step

explnation of the mechanism step by step

Organic Chemistry
Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter17: Alcohols And Phenols
Section17.SE: Something Extra
Problem 67AP: Dehydration of trans-2-methylcyclopentanol with POCl3 in pyridine yields predominantly...
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9 H® From water Sodium borohydride is An mild reducing Agent whivh converts Aldehydes and ketones to Alcohols. Step 2 Ps as . Jollous The mechanism requion atep1 Hyduide Trans Fer (attauk) ONat Na H- B-H H -> NO2 átepa: Abs hraution CH 20H H. ONa NO? 130
Transcribed Image Text:9 H® From water Sodium borohydride is An mild reducing Agent whivh converts Aldehydes and ketones to Alcohols. Step 2 Ps as . Jollous The mechanism requion atep1 Hyduide Trans Fer (attauk) ONat Na H- B-H H -> NO2 átepa: Abs hraution CH 20H H. ONa NO? 130
Reduction of 4-Nitrobenzaldehyde to 4-Nitrobenzyl Alcohol and Thin Layer Chromatography Background. Oxidation and reduction are among the most common organic reactions, both in the laboratory and in biochemical processes. There are literally dozens of different methods of oxidizing alcohols to ketones or aldehydes, and almost as many to reduce ketones or aldehydes back to alcohols. In this experiment, we will be using one of the most common reducing agents, sodium borohydride, to reduce 4-nitrobenzaldehyde to 4-nitrobenzyl alcohol. Note that sodium borohydride is not able to reduce the nitro group to the corresponding amine. The reaction occurs via a nucleophilic attack of the hydride on the carbonyl group. (See Karty, Chapter 17, page 821.) H. CH2OH NaBH4 (1) NO2 When running a chemical reaction, it is important to know when the reaction is complete. This information can prevent you from stopping a reaction too early or wasting time waiting for a reaction to finish. So how can you easily monitor the progress of the reaction, without using up most of the contents of the reaction mixture for NMR analyses? By far the most common technique used is Thin Layer Chromatography (TLC). Generally, TLC is a simple, effective and inexpensive method for separating and analyzing a mixture of compounds (such as the one that may be present half way through the reduction) using only a very small amount of the sample – less than a milligram. TLC is a qualitative technique. It does not give you information on how much of a given compound is in a sample. For details on how Thin Layer Chromatography works, see your lab text. You must read this section prior to performing this experiment.
Transcribed Image Text:Reduction of 4-Nitrobenzaldehyde to 4-Nitrobenzyl Alcohol and Thin Layer Chromatography Background. Oxidation and reduction are among the most common organic reactions, both in the laboratory and in biochemical processes. There are literally dozens of different methods of oxidizing alcohols to ketones or aldehydes, and almost as many to reduce ketones or aldehydes back to alcohols. In this experiment, we will be using one of the most common reducing agents, sodium borohydride, to reduce 4-nitrobenzaldehyde to 4-nitrobenzyl alcohol. Note that sodium borohydride is not able to reduce the nitro group to the corresponding amine. The reaction occurs via a nucleophilic attack of the hydride on the carbonyl group. (See Karty, Chapter 17, page 821.) H. CH2OH NaBH4 (1) NO2 When running a chemical reaction, it is important to know when the reaction is complete. This information can prevent you from stopping a reaction too early or wasting time waiting for a reaction to finish. So how can you easily monitor the progress of the reaction, without using up most of the contents of the reaction mixture for NMR analyses? By far the most common technique used is Thin Layer Chromatography (TLC). Generally, TLC is a simple, effective and inexpensive method for separating and analyzing a mixture of compounds (such as the one that may be present half way through the reduction) using only a very small amount of the sample – less than a milligram. TLC is a qualitative technique. It does not give you information on how much of a given compound is in a sample. For details on how Thin Layer Chromatography works, see your lab text. You must read this section prior to performing this experiment.
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