2-chloro-2-methylpropane

Definition

2-chloro-2-methylpropane, also known as tert-butyl chloride, is an organic compound with the chemical formula (CH3)3CCl. It is a polar molecule that is used in various organic reactions, particularly in the context of addition reactions and Markovnikov's rule.

5 Must Know Facts For Your Next Test

1. 2-chloro-2-methylpropane is a polar molecule due to the unequal distribution of electrons between the carbon-chlorine bond.
2. The addition of hydrobromic acid (HBr) to ethylene is an example of a polar reaction, where the electrophilic bromine atom adds to the less substituted carbon of the double bond.
3. Markovnikov's rule states that in an electrophilic addition reaction, the electrophile will add to the carbon atom that can best stabilize the resulting carbocation intermediate.
4. In the case of 2-chloro-2-methylpropane, the tertiary carbocation intermediate is more stable than the primary carbocation, making the addition of HBr to this molecule a Markovnikov-type reaction.
5. The presence of the chloro and methyl substituents on the 2-carbon of 2-chloro-2-methylpropane contributes to the stability of the tertiary carbocation intermediate, in accordance with Markovnikov's rule.

Review Questions

• Explain how the polarity of 2-chloro-2-methylpropane is related to the addition of HBr to ethylene, a polar reaction.
  • The polarity of 2-chloro-2-methylpropane, arising from the unequal distribution of electrons in the carbon-chlorine bond, is relevant to the discussion of the addition of HBr to ethylene, which is an example of a polar reaction. In a polar reaction, the electrophilic species (in this case, the bromine atom from HBr) selectively adds to the carbon atom that can best stabilize the resulting carbocation intermediate. The polarity of 2-chloro-2-methylpropane, while not directly involved in the ethylene reaction, helps illustrate the concept of polar reactions and the factors that influence their mechanism and outcome.
• Describe how Markovnikov's rule applies to the addition of HBr to 2-chloro-2-methylpropane, and explain the role of the substituents in stabilizing the carbocation intermediate.
  • Markovnikov's rule states that in an electrophilic addition reaction, the electrophile will add to the carbon atom that can best stabilize the resulting carbocation intermediate. In the case of 2-chloro-2-methylpropane, the addition of HBr would result in the formation of a tertiary carbocation intermediate, which is more stable than the primary carbocation that would form if the electrophile added to the other carbon. The presence of the chloro and methyl substituents on the 2-carbon of 2-chloro-2-methylpropane contributes to the stability of the tertiary carbocation intermediate, making this a Markovnikov-type reaction. The stabilization of the carbocation intermediate is a key factor in determining the orientation of the electrophilic addition, as outlined by Markovnikov's rule.
• Analyze how the polarity of 2-chloro-2-methylpropane and the principles of Markovnikov's rule work together to predict the outcome of the addition of HBr to this molecule.
  • The polarity of 2-chloro-2-methylpropane, stemming from the unequal distribution of electrons in the carbon-chlorine bond, is an important factor in understanding the addition of HBr to this molecule. Markovnikov's rule states that in an electrophilic addition reaction, the electrophile (in this case, the bromine atom from HBr) will add to the carbon atom that can best stabilize the resulting carbocation intermediate. In the case of 2-chloro-2-methylpropane, the presence of the chloro and methyl substituents on the 2-carbon atom allows for the formation of a more stable tertiary carbocation intermediate, in accordance with Markovnikov's rule. The polarity of the molecule, while not directly involved in the reaction mechanism, provides the context for understanding the relevance of Markovnikov's rule and how it can be used to predict the outcome of the addition of HBr to 2-chloro-2-methylpropane.

Related terms

Polar Reaction:

A chemical reaction in which the distribution of electrons between atoms is unequal, resulting in the formation of partial positive and negative charges.

Electrophilic Addition:

A type of organic reaction where an electrophile (a species attracted to electrons) adds to a carbon-carbon double bond, forming a new single bond.

Markovnikov's Rule:

A rule that predicts the orientation of an electrophilic addition reaction, stating that the electrophile will add to the carbon atom that can best stabilize the resulting carbocation intermediate.