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Chapter 15: Problem 63

Draw all amines with the formula \(\mathrm{C}_{4} \mathrm{H}_{11} \mathrm{~N}\).

Short Answer

Expert verified
Possible amines are: Primary: butan-1-amine, butan-2-amine, 2-methylpropan-1-amine Secondary: N-methylpropylamine, N-ethylmethylamine Tertiary: trimethylamine, ethyldimethylamine, N-methylethylamine.

Step by step solution

01

Understanding the Formula

The formula \(\mathrm{C}_{4}\mathrm{H}_{11}\mathrm{~N}\) represents an amine with 4 carbon atoms, 11 hydrogen atoms, and 1 nitrogen atom. Amines are organic compounds derived from ammonia by the replacement of hydrogen atoms with alkyl or aryl groups.
02

Categorization of Amines

Amines can be primary (one alkyl group attached to the nitrogen), secondary (two alkyl groups attached), or tertiary (three alkyl groups attached). For this exercise, explore all possible structures for primary, secondary, and tertiary amines with the given formula.
03

Drawing Primary Amines

Primary amines have the structure \(\mathrm{R}-\mathrm{NH}_{2}\). Consider different ways to arrange the 4 carbon atoms (as a straight chain and as branched chains) and place the \(\mathrm{NH}_{2}\) group: 1. Butan-1-amine (n-butylamine): \mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CH}_2-\mathrm{CH}_2\mathrm{NH}_2\2. Butan-2-amine (sec-butylamine): \mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CH}(\text{\mathrm{NH}_2})-\mathrm{CH}_3\3. 2-Methylpropan-1-amine (isobutylamine): \mathrm{(CH}_3)_2\mathrm{CH}-\mathrm{CH}_2-\mathrm{NH}_2\4. 2-Methylpropan-2-amine (tert-butylamine): \mathrm{(CH}_3)_3 \text{C-NH}_2\
04

Drawing Secondary Amines

Secondary amines have the structure \(\mathrm{R}_2\mathrm{NH}\). Explore all combinations of four carbon atoms split between two alkyl groups: 1. N-methylpropylamine: \mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CH}_2-\mathrm{NH}-\mathrm{CH}_3\2. N-ethylmethylamine: \mathrm{CH}_3-\mathrm{NH}-\mathrm{CH}_2-\mathrm{CH}_3\3. N-dimethylisopropylamine: \mathrm{(CH}_3)_2\mathrm{CH}-\text{NH}-\mathrm{CH}_3\4. N-ethylisopropylamine: \mathrm{(CH}_3)_{2}\mathrm{CH}-\text{NH}-\mathrm{C}_2\mathrm{H}_5\
05

Drawing Tertiary Amines

Tertiary amines have the structure \(\mathrm{R}_3\mathrm{N}\). Ensure the total number of carbons split among three groups equals four: 1. trimethylamine: \mathrm{(CH}_3)_3\mathrm{N}\2. ethyldimethylamine: \mathrm{(CH}_3)_2-\mathrm{N}-\mathrm{CH}_2-\mathrm{CH}_3\3. N-methylethylamine: \mathrm{(CH}_3)(\mathrm{CH}_3-\mathrm{CH}_2-)-\mathrm{N}-\mathrm{CH}_3\

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Key Concepts

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

Primary Amines
A primary amine has one alkyl group attached to the nitrogen atom and follows the structure \(\mathrm{R-NH}_2\). For the formula \(\mathrm{C}_4\mathrm{H}_{11}\mathrm{N}\), we have different ways to arrange the 4 carbon atoms with the \(\mathrm{NH}_2\) group attached at various positions.
Here are the primary amines for \(\mathrm{C}_4\mathrm{H}_{11}\mathrm{N}\):
  • Butan-1-amine (n-butylamine): This has a straight chain of 4 carbons with the \(\mathrm{NH}_2\) group at the end: \(\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CH}_2-\mathrm{CH}_2\mathrm{NH}_2\).
  • Butan-2-amine (sec-butylamine): Similar to Butan-1-amine but the \(\mathrm{NH}_2\) group is on the second carbon: \(\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CH}(\mathrm{NH}_2)-\mathrm{CH}_3\).
  • 2-Methylpropan-1-amine (isobutylamine): This structure has a branching carbon (methyl group) attached to the second carbon: \((\mathrm{CH}_3)_2-\mathrm{CH}-\mathrm{CH}_2-\mathrm{NH}_2\).
  • 2-Methylpropan-2-amine (tert-butylamine): Here, all four carbons are centered with the \(\mathrm{NH}_2\) group at the central carbon: \((\mathrm{CH}_3)_3-\mathrm{C-NH}_2\).

This variety gives us a good idea of how primary amines can differ based on their structure.
Secondary Amines
Secondary amines have the formula \(\mathrm{R}_2\mathrm{NH}\), meaning two alkyl groups are attached to the nitrogen. For \(\mathrm{C}_4\mathrm{H}_{11}\mathrm{N}\), the total number of carbons in the alkyl groups and the nitrogen's hydrogen must be four. Let's explore the possibilities:
  • N-methylpropylamine: The structure involves a methyl group (one carbon) and a propyl group (three carbons) attached to the nitrogen: \(\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CH}_2-\mathrm{NH}-\mathrm{CH}_3\).
  • N-ethylmethylamine: Here, a methyl group and an ethyl group (two carbons) are bonded to the nitrogen: \(\mathrm{CH}_3-\mathrm{NH}-\mathrm{CH}_2-\mathrm{CH}_3\).
  • N-dimethylisopropylamine: Combining a dimethyl group with an isopropyl group creates this structure: \((\mathrm{CH}_3)_2\mathrm{CH}-\mathrm{NH}-\mathrm{CH}_3\).
  • N-ethylisopropylamine: This configuration has an isopropyl and an ethyl group attached to the nitrogen: \((\mathrm{CH}_3)_2-\mathrm{CH}-\mathrm{NH}-\mathrm{C}_2\mathrm{H}_5\).

These varied structures demonstrate the flexibility in forming secondary amines, where the key is to balance the number of carbons in the two alkyl groups.
Tertiary Amines
Tertiary amines are formed when three alkyl groups are attached to the nitrogen atom, leading to the structure \(\mathrm{R}_3\mathrm{N}\). For \(\mathrm{C}_4\mathrm{H}_{11}\mathrm{N}\), the three alkyl groups' total carbons must equal four. Here are the possible tertiary amines for the given formula:
  • Trimethylamine: This has three methyl groups (one carbon each) attached to the nitrogen: \((\mathrm{CH}_3)_3\mathrm{N}\).
  • Ethyldimethylamine: This configuration involves two methyl groups and one ethyl group attached to the nitrogen: \((\mathrm{CH}_3)_2-\mathrm{N}-\mathrm{CH}_2-\mathrm{CH}_3\).
  • N-methylethylamine: This has one methyl group and an ethyl group directly linked to another methyl, making it: \((\mathrm{CH}_3)(\mathrm{CH}_3-\mathrm{CH}_2-)-\mathrm{N}-\mathrm{CH}_3\).

Understanding these structures showcases how tertiary amines can have various configurations based on how the carbon atoms are distributed among the three alkyl groups.

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Most popular questions from this chapter

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