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Chapter 16: Problem 20

How would you convert \(N\) -ethylbenzamide to each of the following products? (a) Benzoic acid (b) Benzyl alcohol (c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{NHCH}_{2} \mathrm{CH}_{3}\)

Short Answer

Expert verified
(a) Hydrolysis to benzoic acid. (b) Hydrolysis followed by reduction to benzyl alcohol. (c) Hydrolysis, reduction, chlorination, then substitution to C鈧咹鈧匔H鈧侼HCH鈧侰H鈧�.

Step by step solution

01

Hydrolysis to Benzoic Acid

To convert N-ethylbenzamide to benzoic acid, perform acidic or basic hydrolysis. Under acidic conditions, heat N-ethylbenzamide with hydrochloric acid (HCl) or sulfuric acid (H鈧係O鈧�). This will hydrolyze the amide bond, resulting in the formation of benzoic acid and ethanol. Alternatively, for basic hydrolysis, use sodium hydroxide (NaOH) followed by acidification.
02

Reduction to Benzyl Alcohol

To obtain benzyl alcohol from N-ethylbenzamide, first perform an acid-catalyzed hydrolysis to convert N-ethylbenzamide to benzoic acid. Next, reduce the carboxylic acid using lithium aluminum hydride (LiAlH鈧�). This reducing agent will convert benzoic acid to benzyl alcohol.
03

Preparation of C_6H_5CH_2NHCH_2CH_3

Begin with the hydrolysis of N-ethylbenzamide to benzoic acid. Convert benzoic acid to benzyl alcohol using LiAlH鈧�. Then, convert benzyl alcohol to benzyl chloride using thionyl chloride (SOCl鈧�). Finally, react benzyl chloride with ethylamine (CH鈧僀H鈧侼H鈧�) to form C鈧咹鈧匔H鈧侼HCH鈧侰H鈧� through nucleophilic substitution.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Hydrolysis
Hydrolysis is a fundamental chemical reaction where water breaks down a compound. This process is crucial in organic chemistry for breaking bonds in various molecules.
In the context of converting N-ethylbenzamide, hydrolysis can be achieved under acidic or basic conditions.
When N-ethylbenzamide undergoes hydrolysis, the amide bond is cleaved. This results in two products: benzoic acid and ethanol.
  • Acidic hydrolysis involves heating the amide with strong acids like hydrochloric acid (HCl) or sulfuric acid (H鈧係O鈧�).
  • For basic hydrolysis, sodium hydroxide (NaOH) is used followed by acidification.
The choice between acidic or basic hydrolysis depends on the desired reaction conditions and potential by-products.
Acid-Base Reaction
An acid-base reaction is an essential type of chemical reaction where an acid reacts with a base to produce a salt and often water. This interaction is characterized by the transfer of protons.
In the hydrolysis step for converting N-ethylbenzamide, using a base like NaOH can lead to an initial reaction forming sodium benzoate as an intermediate.
This results from the basic solution deprotonating the benzoic acid product. Subsequently, acidification is needed to revert sodium benzoate to benzoic acid, making the reaction complete.
  • The basic environment assists in breaking the amide bond effectively.
  • After the formation of sodium benzoate, adding an acid (like HCl) ensures the regeneration of benzoic acid.
Understanding the mechanism of acid-base reactions aids in predicting the outcomes of such transformations.
Reduction Process
Reduction is a chemical reaction that involves the gain of electrons or removal of oxygen from a molecule. It's the opposite of oxidation and is vital for various organic conversions.
To transform N-ethylbenzamide into benzyl alcohol, reduction follows hydrolysis to first form benzoic acid.
The reducing agent, lithium aluminum hydride (LiAlH鈧�), effectively converts carboxylic acids like benzoic acid into alcohols.
  • LiAlH鈧� is highly reactive and useful for reducing strong bonds in carboxylic acids.
  • During this reduction, benzoic acid loses an oxygen atom, leading to the formation of benzyl alcohol.
Reduction processes are key in converting more oxidized forms of molecules into their simpler, often more reactive, alcohol forms.
Nucleophilic Substitution
Nucleophilic substitution is a reaction where a nucleophile, an electron-rich entity, replaces a leaving group in a molecule.
For obtaining C鈧咹鈧匔H鈧侼HCH鈧侰H鈧�, nucleophilic substitution allows for the interaction between benzyl chloride and ethylamine.
This step follows the preparation of benzyl chloride from benzyl alcohol using thionyl chloride (SOCl鈧�).
  • A chloride ion (Cl鈦�) serves as the leaving group from benzyl chloride.
  • Ethylamine, as a nucleophile, attacks the benzyl site, replacing the Cl鈦� ion.
This mechanism is central to forming new bonds and synthesizing complex molecules in organic chemistry.
Organic Chemistry Reactions
Organic chemistry involves a wide range of reactions that facilitate the conversion and synthesis of organic compounds. These reactions are integral for creating complex chemical structures.
In the transformation of N-ethylbenzamide, several organic reactions come into play:
  • Hydrolysis: Converts amides to acids under various conditions.
  • Reduction: Utilizes agents like LiAlH鈧� for reducing molecules to alcohols.
  • Nucleophilic substitution: Facilitates bond formation through the exchange of atoms.
Each of these reactions demonstrates the richness and versatility of organic transformations, showcasing their significance in producing new materials and pharmaceuticals. Understanding these processes is essential in harnessing their power for practical applications.

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Most popular questions from this chapter

The following reactivity order has been found for the saponification of \(p\) -substituted methyl benzoates: $$ \mathrm{Y}=\mathrm{NO}_{2}>\mathrm{Br}>\mathrm{H}>\mathrm{CH}_{3}>\mathrm{OCH}_{3} $$ How can you explain this reactivity order? Where would you expect \(\mathrm{Y}=\mathrm{CHO}\) and \(\mathrm{Y}=\mathrm{NH}_{2}\) to be in the reactivity list?

Yesterday's drug can be today's poison. Cocaine enjoyed a much better reputation 100 years ago, when it was used as a stimulant in many products (including Coca-Cola) as well as in drops to treat toothaches and depression. What three molecules are produced by hydrolysis of cocaine?

Draw structures corresponding to the following names: (a) Phenyl benzoate (b) \(N\) -Ethyl- \(N\) -methylbutanamide (c) 2,4 -Dimethylpentanoyl chloride (d) Methyl 1-methylcyclohexanecarboxylate (e) Ethyl 3-oxopentanoate (f) Methyl \(p\) -bromothiobenzoate (g) Formic propanoic anhydride (h) cis-2-Methylcyclopentanecarbonyl bromide

How might you prepare the following esters using a nucleophilic acyl substitution reaction of an acid chloride? (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{CH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) (c) Ethyl benzoate

Draw structures of the step-growth polymers you would expect to obtain from the following reactions: $$ \text { (a) } \mathrm{BrCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}+\mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH} \quad \stackrel{\text { Base }}{\longrightarrow} ? $$ $$ \text { (b) } \mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{OH}+\mathrm{HO}_{2} \mathrm{C}\left(\mathrm{CH}_{2}\right)_{6} \mathrm{CO}_{2} \mathrm{H} \quad \stackrel{\mathrm{H}_{2} \mathrm{SO}_{4} \text { catalyst }}{\longrightarrow} ? $$ $$ \text { (c) } $$
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