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Chapter 17: Problem 76

Why can't the molecule 2,2 -dimethyl-1-butene exist?

Short Answer

Expert verified
2,2-dimethyl-1-butene cannot exist because, according to its IUPAC name, it should have two methyl groups on the second carbon and a double bond between carbon #1 and #2. Upon attempting to draw and analyze the structure, it becomes clear that what was believed to be 2,2-dimethyl-1-butene is actually 3,3-dimethyl-1-butene. Therefore, 2,2-dimethyl-1-butene cannot exist as a valid chemical structure.

Step by step solution

01

1. Identify the parent hydrocarbon

The base name 'butene' tells us that we are dealing with a 4-carbon alkene - a hydrocarbon with a carbon-carbon double bond. Four carbons in a straight chain form a butene molecule and will have the double bond between carbon #1 and #2 or carbon #2 and #3, resulting in structural isomers: 1-Butene: H2C=CH-CH2-CH3 2-Butene: CH3-CH=CH-CH3.
02

2. Analyze the substituents

In this case, we are asked to consider 2,2-dimethyl-1-butene. The name indicates that there should be two methyl groups (CH3) that are attached to the second carbon of the parent alkene.
03

3. Attempt to Draw the Molecule of 2,2-dimethyl-1-butene

We can attempt to draw the assumed structure of 2,2-dimethyl-1-butene based on its name: H2C=CH-CH(CH3)2 (1-butene with 2 methyl groups attached to the second carbon)
04

4. Analyze the Structure

When the two methyl groups are attached to the second carbon atom, it becomes clear that the carbon-carbon double bond now exists between the first and third carbon atoms. As a result, the structure for 2,2-dimethyl-1-butene is actually: H2C=CH-CH(CH3)2 However, this molecule is actually 3,3-dimethyl-1-butene. So we can see that given the provided name and attempted structure, it is impossible to have a real molecule of 2,2-dimethyl-1-butene.
05

5. Conclusion

2,2-dimethyl-1-butene cannot exist because according to its IUPAC name, it would have two methyl groups on the second carbon and a double bond between carbon #1 and #2. Upon attempting to draw and analyze the structure, it becomes clear that what was believed to be 2,2-dimethyl-1-butene would actually be 3,3-dimethyl-1-butene. Therefore, 2,2-dimethyl-1-butene cannot exist as a valid chemical structure.

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Most popular questions from this chapter

Write an equilibrium to show how a primary amine, \(\mathrm{H}_{2} \mathrm{NR}\), makes water basic. To which side does the equilibrium lie? What does this imply?

Explain why the molecules 1 -hexene, 2 -hexene, and 3 -hexene exist, but the molecules 4 -hexene and 5 -hexene do not.

The alkanes containing one, two, three, and four carbons are gases at room temperature. However, as alkanes get larger, they become liquids and then solids at room temperature. Why?

Explain how hydrocarbons containing an \(\mathrm{NH}_{2}\) group are named.

What is wrong with using common names for hydrocarbon molecules?
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