The following are some other organic reactions covered in...

The following are some other organic reactions covered in Section $21.4 .$ Give an example to illustrate each type of reaction. a. Adding $\mathrm{H}_{2} \mathrm{O}$ to an alkene (in the presence of $\mathrm{H}^{+}$ ) yields an alcohol. b. Primary alcohols are oxidized to aldehydes, which can be further oxidized to carboxylic acids. c. Secondary alcohols are oxidized to ketones. d. Reacting an alcohol with a carboxylic acid (in the presence of $\mathrm{H}^{+}$ ) produces an ester.

The following are some other organic reactions covered in Section $21.4 .$ Give an example to illustrate each type of reaction.
a. Adding $\mathrm{H}_{2} \mathrm{O}$ to an alkene (in the presence of $\mathrm{H}^{+}$ ) yields an alcohol.
b. Primary alcohols are oxidized to aldehydes, which can be further oxidized to carboxylic acids.
c. Secondary alcohols are oxidized to ketones.
d. Reacting an alcohol with a carboxylic acid (in the presence of $\mathrm{H}^{+}$ ) produces an ester.

Key Concepts

Fischer Esterification

Fischer esterification is a practical method for synthesizing esters from an alcohol and a carboxylic acid in the presence of an acid catalyst. The reaction progresses via a nucleophilic addition followed by the elimination of water, forming an ester linkage. It is generally an equilibrium reaction, and the yield is often increased by removing water or using an excess of one of the reactants.

Secondary Alcohol Oxidation

In the oxidation of secondary alcohols, the loss of two hydrogen atoms results in the formation of a ketone. Unlike primary alcohol oxidation, secondary alcohols do not have the ability to form aldehydes and further oxidize because the carbon atom is bonded to two other carbons, favoring the single-step oxidation to ketones. This reaction also depends on the type and strength of the oxidizing agent used.

Primary Alcohol Oxidation

The oxidation of primary alcohols is a reaction that converts them first into aldehydes and can further oxidize them into carboxylic acids. This reaction involves the removal of hydrogen atoms from the alcohol, and the transformation is dependent on the nature of the oxidizing agent. Milder oxidizing agents tend to stop at the aldehyde stage, whereas stronger oxidizers drive the reaction all the way to carboxylic acids.

Acid-Catalyzed Hydration

This reaction involves the addition of water to a carbon-carbon double bond (alkene) in the presence of an acid catalyst. The mechanism starts with the protonation of the alkene, forming a carbocation intermediate. Water then acts as a nucleophile, attacking the carbocation to form an oxonium ion, which is deprotonated to yield an alcohol. This process typically follows Markovnikov's rule, where the hydrogen attaches to the carbon with the most hydrogens already attached.

Transcript

00:07 This question asks us to give some examples of organic reactions covered in the chapter.

00:13 So the first one is adding water to an alken with acid present yields in alcohol.

00:18 So we'll do an example of this.

00:20 I'm going to use propine here.

00:25 So if we have propine and we have water with some acid present, this is going to add an alcohol on and we're going to put the alcohol on the most substituted carbons so the one right in the middle, and we'll add an h from the acid onto the other carbon from the double bond to give each carbon four bonds.

00:45 So that is an example of what is called acid catalyzed hydration.

00:51 And then for part b, we have primary alcohols can be oxidized to elbehydes, and then further oxidized to carboxylic acids.

01:01 So let's use a primary alcohol.

01:05 Let's use propanol.

01:09 And so they can be oxidized first to an aldehyde.

01:12 So we can do this.

01:14 There are certain reagents that will only go to an alohydehyde and won't go to all the way to a carbosylic acid.

01:20 An example of that is pcc.

01:22 So that will give us an aldehyde only.

01:28 And then we can oxidize that further to a carboxylic acid using h2 -c -r -o -7.

01:36 Chromic acid is a really strong oxidizing agent, so that will give us a carbonsilic acid that would look like this.

01:44 Or we can go just directly to the carboxylic acid.

01:49 It will still go through the aldehyde, but you can do go all the way from the alcohol to the carboxylic acid with just one region if you just use the chromic acid from the beginning.

01:59 So that is our example for part b...

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