Which of the following alkanes contains primary ($1^\circ$), tertiary ($3^\circ$), and quaternary ($4^\circ$) carbons, but no secondary ($2^\circ$) carbons?
2,2,3-Trimethylbutane
This question asks us to identify a specific alkane from a list that contains primary ($1^\circ$), tertiary ($3^\circ$), and quaternary ($4^\circ$) carbon atoms, while excluding any secondary ($2^\circ$) carbon atoms. Let's break down how to determine the type of each carbon atom in an alkane and then analyze each given option.
In organic chemistry, carbon atoms in alkane structures are classified based on the number of other carbon atoms they are directly bonded to:
We need to find the alkane structure that has all three types ($1^\circ$, $3^\circ$, $4^\circ$) and none of the secondary ($2^\circ$) type.
Let's examine the structure and carbon types for each option.
The structure of 2,3-Dimethylpentane is:
$CH_3 - CH(CH_3) - CH(CH_3) - CH_2 - CH_3$
Let's identify the types of carbons:
Carbon types present: $1^\circ$, $2^\circ$, $3^\circ$. This structure contains a secondary ($2^\circ$) carbon, so it does not meet the criteria.
The structure of 2,2-Dimethylpentane is:
$CH_3 - C(CH_3)_2 - CH_2 - CH_2 - CH_3$
Let's identify the types of carbons:
Carbon types present: $1^\circ$, $2^\circ$, $4^\circ$. This structure contains secondary ($2^\circ$) carbons, so it does not meet the criteria.
The structure of 3-Ethyl-2-methylpentane is:
$CH_3 - CH(CH_3) - CH(CH_2CH_3) - CH_2 - CH_3$
Let's identify the types of carbons:
Carbon types present: $1^\circ$, $2^\circ$, $3^\circ$. This structure contains secondary ($2^\circ$) carbons, so it does not meet the criteria.
The structure of 2,2,3-Trimethylbutane is:
$CH_3 - C(CH_3)_2 - CH(CH_3) - CH_3$
Let's identify the types of carbons:
Carbon types present: $1^\circ$, $3^\circ$, $4^\circ$. This structure contains primary ($1^\circ$), tertiary ($3^\circ$), and quaternary ($4^\circ$) carbons, and crucially, it contains no secondary ($2^\circ$) carbons.
By analyzing the structure and classifying the carbon atoms in each option, we found that 2,2,3-Trimethylbutane is the only alkane that satisfies the condition of containing primary ($1^\circ$), tertiary ($3^\circ$), and quaternary ($4^\circ$) carbons, while having no secondary ($2^\circ$) carbons.
Here is a summary table:
| Alkane Name | Structure | $1^\circ$ Carbons | $2^\circ$ Carbons | $3^\circ$ Carbons | $4^\circ$ Carbons | Meets Criteria? |
|---|---|---|---|---|---|---|
| 2,3-Dimethylpentane | $CH_3-CH(CH_3)-CH(CH_3)-CH_2-CH_3$ | Yes (5) | Yes (1) | Yes (2) | No | No |
| 2,2-Dimethylpentane | $CH_3-C(CH_3)_2-CH_2-CH_2-CH_3$ | Yes (5) | Yes (2) | No | Yes (1) | No |
| 3-Ethyl-2-methylpentane | $CH_3-CH(CH_3)-CH(CH_2CH_3)-CH_2-CH_3$ | Yes (6) | Yes (2) | Yes (2) | No | No |
| 2,2,3-Trimethylbutane | $CH_3-C(CH_3)_2-CH(CH_3)-CH_3$ | Yes (6) | No | Yes (1) | Yes (1) | Yes |
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