Tert-Butyl chloride

Definition

tert-Butyl chloride, also known as 2-chloro-2-methylpropane, is an organic compound with the chemical formula (CH3)3CCl. It is a colorless, volatile liquid that is used as a building block in the synthesis of various organic compounds and as a solvent in certain applications.

5 Must Know Facts For Your Next Test

1. tert-Butyl chloride is a tertiary alkyl halide, meaning the carbon atom bearing the chlorine is bonded to three other carbon atoms.
2. Due to the bulky nature of the tert-butyl group, tert-Butyl chloride exhibits significant steric hindrance, which can impact its reactivity in SN2 reactions.
3. The presence of the three methyl groups attached to the central carbon atom in tert-Butyl chloride makes the carbon atom less susceptible to nucleophilic attack in an SN2 reaction, as the bulky groups hinder the approach of the nucleophile.
4. The steric hindrance in tert-Butyl chloride also leads to a slower rate of reaction in SN2 reactions compared to primary or secondary alkyl halides.
5. The tertiary nature of the carbon atom in tert-Butyl chloride makes the C-Cl bond more polarized, which can influence the reactivity of the compound in certain reactions.

Review Questions

• Explain how the tertiary nature of tert-Butyl chloride affects its reactivity in SN2 reactions.
  • The tertiary nature of tert-Butyl chloride, where the carbon atom bearing the chlorine is bonded to three other carbon atoms, creates significant steric hindrance around the carbon. This steric hindrance makes it more difficult for a nucleophile to approach the carbon atom and displace the chlorine in an SN2 reaction. As a result, tert-Butyl chloride typically exhibits a slower rate of reaction in SN2 processes compared to primary or secondary alkyl halides, where the steric hindrance is less pronounced.
• Describe the impact of the tert-Butyl group on the polarity of the C-Cl bond in tert-Butyl chloride.
  • The presence of the three methyl groups in the tert-Butyl group of tert-Butyl chloride makes the carbon atom more electropositive, leading to a greater polarization of the C-Cl bond. This increased polarity can influence the reactivity of tert-Butyl chloride in certain reactions, as the more polarized C-Cl bond may be more susceptible to nucleophilic attack or other transformations. The degree of bond polarization can affect the overall reactivity and behavior of tert-Butyl chloride in organic synthesis and related applications.
• Evaluate how the steric hindrance in tert-Butyl chloride would impact its ability to undergo an SN2 reaction with a bulky nucleophile compared to a smaller nucleophile.
  • The significant steric hindrance around the carbon atom in tert-Butyl chloride, due to the presence of the three methyl groups, would greatly impede the ability of a bulky nucleophile to approach and displace the chlorine atom in an SN2 reaction. The bulky nature of the nucleophile would further exacerbate the steric effects, making the SN2 reaction with tert-Butyl chloride much less favorable. In contrast, a smaller nucleophile would be able to approach the carbon atom more easily, allowing the SN2 reaction to proceed, albeit at a slower rate compared to primary or secondary alkyl halides. The interplay between the steric hindrance of the tert-Butyl group and the size of the nucleophile is a critical factor in determining the feasibility and rate of SN2 reactions involving tert-Butyl chloride.

Related terms

SN2 Reaction:

The SN2 reaction, or bimolecular nucleophilic substitution, is a type of organic reaction in which a nucleophile attacks the backside of a carbon atom bearing a good leaving group, resulting in the displacement of the leaving group and the inversion of stereochemistry.

Tertiary Alkyl Halides:

Tertiary alkyl halides are organic compounds in which a halogen atom (such as chlorine) is attached to a tertiary carbon atom, which is a carbon atom bonded to three other carbon atoms.

Steric Hindrance:

Steric hindrance, also known as steric strain or steric effects, refers to the repulsive forces that arise when atoms or groups of atoms are forced into close proximity, which can affect the stability and reactivity of molecules.