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Chapter 22: Problem 9

Give an example reaction that would yield the following products as major organic products. See Exercises 22.68 and 22.71 for some hints. For oxidation reactions, just write oxidation over the arrow and don’t worry about the actual reagent. a. primary alcohol b. secondary alcohol c. tertiary alcohol d. aldehyde e. ketone f. carboxylic acid g. ester

Short Answer

Expert verified
a. Primary alcohol: \( HCHO + [ LiAlH_4 ] \rightarrow CH_3OH \) b. Secondary alcohol: \( CH_3COCH_3 + [ LiAlH_4 ] \rightarrow CH_3CH(OH)CH_3 \) c. Tertiary alcohol: \( CH_3C(CH_3)=CH_2 + H_2O \xrightarrow{ H_2SO_4 } CH_3C(CH_3)(CH_2)(OH) \) d. Aldehyde: \( CH_3CH_2OH \xrightarrow{ oxidation } CH_3CHO \) e. Ketone: \( CH_3CH(OH)CH_3 \xrightarrow{ oxidation } CH_3COCH_3 \) f. Carboxylic acid: \( CH_3CH_2OH \xrightarrow{ oxidation } CH_3COOH \) g. Ester: \( CH_3COOH + CH_3OH \xrightarrow{ H_2SO_4 } CH_3COOCH_3 + H_2O \)

Step by step solution

01

Primary alcohol

Reduction of an aldehyde is a common method to prepare primary alcohols. We can use a simple aldehyde such as formaldehyde (\( HCHO\) ) with a reducing agent like lithium aluminium hydride (\( LiAlH_4 \)). \[ HCHO + [ LiAlH_4 ] \rightarrow CH_3OH \]
02

Secondary alcohol

Reduction of a ketone is a common method to prepare secondary alcohols. We can use a simple ketone such as acetone (\( CH_3-CO-CH_3 \)) and a reducing agent like lithium aluminium hydride (\( LiAlH_4 \)). \[ CH_3COCH_3 + [ LiAlH_4 ] \rightarrow CH_3CH(OH)CH_3 \]
03

Tertiary alcohol

The reaction of an alkene with water in the presence of an acid catalyst (hydration reaction) can produce tertiary alcohols. We can use a simple alkene such as 2-methylpropene (\( CH_3C(CH_3)=CH_2\)) and a dilute sulfuric acid solution (\( H_2SO_4 \)). \[ CH_3C(CH_3)=CH_2 + H_2O \xrightarrow{ H_2SO_4 } CH_3C(CH_3)(CH_2)(OH) \]
04

Aldehyde

A common method to produce an aldehyde is by the partial oxidation of a primary alcohol. We can use a simple primary alcohol like ethanol (\( CH_3CH_2OH \)) and an oxidation reagent. \[ CH_3CH_2OH \xrightarrow{ oxidation } CH_3CHO \]
05

Ketone

The oxidation of a secondary alcohol results in a ketone. We can use a simple secondary alcohol like isopropanol (\( CH_3CH(OH)CH_3 \)) and an oxidation reagent. \[ CH_3CH(OH)CH_3 \xrightarrow{ oxidation } CH_3COCH_3 \]
06

Carboxylic acid

Complete oxidation of a primary alcohol can generate a carboxylic acid. We can use a simple primary alcohol like ethanol (\( CH_3CH_2OH \)) and an oxidation reagent. \[ CH_3CH_2OH \xrightarrow{ oxidation } CH_3COOH \]
07

Ester

The reaction of a carboxylic acid with an alcohol in the presence of an acid catalyst (esterification reaction) produces esters. We can use a simple carboxylic acid like acetic acid (\( CH_3COOH \)) and a simple alcohol like methanol (\( CH_3OH \)) with a sulfuric acid catalyst. \[ CH_3COOH + CH_3OH \xrightarrow{ H_2SO_4 } CH_3COOCH_3 + H_2O \]

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Most popular questions from this chapter

Which of the following polymers would be stronger or more rigid? Explain your choices. a. The copolymer of ethylene glycol and terephthalic acid or the copolymer of \(1,2\) -diaminoethane and terephthalic acid $\left(1,2 \text { -diaminoethane }=\mathrm{NH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}\right)$ b. The polymer of \(\mathrm{HO}-\left(\mathrm{CH}_{2}\right)_{6}-\mathrm{CO}_{2} \mathrm{H}\) or that of c. Polyacetylene or polyethylene (The monomer in polyacetylene is ethyne.)

All amino acids have at least two functional groups with acidic or basic properties. In alanine, the carboxylic acid group has $K_{a}=4.5 \times 10^{-3}\( and the amino group has \)K_{b}=7.4 \times 10^{-5} .$ Three ions of alanine are possible when alanine is dissolved in water. Which of these ions would predominate in a solution with \(\left[\mathrm{H}^{+}\right]=1.0 M ?\) In a solution with \(\left[\mathrm{OH}^{-}\right]=1.0 \mathrm{M} ?\)

When toluene \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{3}\right)\) reacts with chlorine gas in the presence of iron(III) catalyst, the product is a mixture of the ortho and para isomers of $\mathrm{C}_{6} \mathrm{H}_{4} \mathrm{ClCH}_{3}$ . However, when the reaction is light-catalyzed with no \(\mathrm{Fe}^{3+}\) catalyst present, the product is $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{Cl}$ . Explain.

Give an example of a hydrocarbon that, in theory, exhibits each of the following bond angles: \(60^{\circ}, 90^{\circ}, 109.5^{\circ}, 120^{\circ},\) and \(180^{\circ} .\)

Identify each of the following compounds as a carboxylic acid, ester, ketone, aldehyde, or amine. a. Anthraquinone, an important starting material in the manufacture of dyes:
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