Chapter 21: Problem 41
Give the structures of all possible nitrogen-containing organic products that might be expected to form on reaction of chloroethane with ammonia. (Hint: Consider multiple alkylations.)
Short Answer
Expert verified
The possible products are ethylamine, diethylamine, triethylamine, and tetraethylammonium chloride.
Step by step solution
01
Identify the Initial Reactant and Reagent
The initial reactant is chloroethane (C鈧侶鈧匔l) and the reagent is ammonia (NH鈧).
02
Understand the Primary Reaction
In the primary reaction, chloroethane reacts with ammonia to form ethylamine (C鈧侶鈧匩H鈧) and HCl. This is a nucleophilic substitution reaction where the chlorine atom is replaced by an amino group.
03
Consider Secondary Alkylation
Ethylamine (C鈧侶鈧匩H鈧) formed in Step 2 can further react with another molecule of chloroethane to form diethylamine (C鈧侶鈧)鈧侼H.
04
Consider Tertiary Alkylation
Diethylamine (C鈧侶鈧)鈧侼H can react with another molecule of chloroethane to form triethylamine (C鈧侶鈧)鈧僋.
05
Consider Quaternary Ammonium Salt Formation
Triethylamine (C鈧侶鈧)鈧僋 can further react with chloroethane to form a quaternary ammonium salt, tetraethylammonium chloride [(C鈧侶鈧)鈧凬鈦篊l鈦籡.
06
Summarize the Products
The possible nitrogen-containing organic products are: 1) ethylamine (C鈧侶鈧匩H鈧), 2) diethylamine (C鈧侶鈧)鈧侼H, 3) triethylamine (C鈧侶鈧)鈧僋, and 4) tetraethylammonium chloride [(C鈧侶鈧)鈧凬鈦篊l鈦籡.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Nucleophilic Substitution
One of the foundational concepts in organic chemistry is nucleophilic substitution. This reaction involves a nucleophile, a molecule with a free pair of electrons, attacking an electrophile, a molecule deficient in electrons. In our exercise, chloroethane (C鈧侶鈧匔l) acts as the electrophile, where the chlorine atom is a leaving group. When ammonia (NH鈧) is the nucleophile, it will attack the carbon atom bonded to the chlorine, replacing the chlorine atom with an amino group to form ethylamine (C鈧侶鈧匩H鈧). This type of reaction is crucial in forming various organic compounds.
Here is a simple breakdown:
Here is a simple breakdown:
- Ammonia attacks the carbon atom bonded with chlorine on chloroethane.
- The chlorine atom leaves, forming ethylamine and releasing HCl.
Alkylation
Alkylation is the process of adding an alkyl group to an organic molecule. In the exercise, after the initial nucleophilic substitution reaction, ethylamine (C鈧侶鈧匩H鈧) formed can undergo further alkylation. This involves multiple steps:
- Ethylamine can react with another molecule of chloroethane to form diethylamine (C鈧侶鈧)鈧侼H.
- Diethylamine can react with another chloroethane molecule to form triethylamine (C鈧侶鈧)鈧僋.
- Triethylamine can react one more time to form tetraethylammonium chloride [(C鈧侶鈧)鈧凬鈦篊l鈦籡.
Amines
Amines are organic compounds derived from ammonia, with one or more hydrogen atoms replaced by alkyl or aryl groups. In the context of our exercise, the initial product formed, ethylamine (C鈧侶鈧匩H鈧), is a primary amine. As further alkylation occurs, secondary and tertiary amines are formed:
- Primary amine: Ethylamine (C鈧侶鈧匩H鈧)
- Secondary amine: Diethylamine (C鈧侶鈧)鈧侼H
- Tertiary amine: Triethylamine (C鈧侶鈧)鈧僋
Quaternary Ammonium Salts
When a tertiary amine reacts with an alkyl halide like chloroethane, it can form a quaternary ammonium salt. For example, triethylamine (C鈧侶鈧)鈧僋 can react with chloroethane to form tetraethylammonium chloride [(C鈧侶鈧)鈧凬鈦篊l鈦籡. This is the final step in our exercise:
- The nitrogen in triethylamine has three ethyl groups and a lone pair of electrons.
- This lone pair attacks chloroethane's carbon, attaching a fourth ethyl group to the nitrogen.
- This forms a positively charged nitrogen atom with four ethyl groups and a chloride anion to balance the charge.