Which of the following statements is true concerning the E2 reactions ...
FI uorine is most electronegative, increases acidity of β-H to the most.
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Which of the following statements is true concerning the E2 reactions ...
Explanation:
E2 reactions involve the elimination of a leaving group and a proton from an adjacent carbon atom. Alkyl fluorides are known to undergo E2 reactions, but there are some important considerations to keep in mind.
B. The transition state of this E2 reaction resembles a carbanion rather than an alkene.
- The transition state of an E2 reaction involves the formation of a new bond between the carbon atom adjacent to the leaving group and the base. In the case of alkyl fluorides, the fluoride ion is the leaving group.
- Fluorine is a highly electronegative atom, which means that the carbon-fluorine bond is quite polarized. As a result, the fluoride ion has a significant negative charge when it leaves, and the carbon atom adjacent to it is left with a significant positive charge.
- This positive charge is stabilized by the electron-withdrawing effect of the fluorine atom, which means that the transition state of the E2 reaction resembles a carbanion rather than an alkene.
- This stabilization makes the E2 reaction of alkyl fluorides more favorable than the E2 reaction of alkyl iodides, for example, which do not have such strong electron-withdrawing groups.
A. Alkyl fluorides do not react more readily in E2 reactions than alkyl iodides.
- While it is true that the E2 reaction of alkyl fluorides is more favorable than that of alkyl iodides, this does not mean that alkyl fluorides react more readily in E2 reactions overall.
- The reactivity of a particular compound in an E2 reaction depends on a variety of factors, including the strength of the carbon-halogen bond, the nature of the leaving group, and the steric hindrance around the carbon atom undergoing elimination.
C. The CF bond is the weakest carbon-halogen bond, but this does not mean that SN2 will always predominate over E2 in the reactions of alkyl fluorides.
- The CF bond is indeed the weakest carbon-halogen bond, but this fact alone does not determine the mechanism of a particular reaction.
- The SN2 and E2 reactions are competing pathways, and the mechanism that predominates depends on a variety of factors, including the nature of the substrate, the strength of the nucleophile/base, and the steric hindrance around the carbon atom undergoing substitution/elimination.
D. Alkyl fluorides do not react to form the most stable carbocation intermediate.
- Carbocation intermediates are not typically formed in E2 reactions, which involve the concerted elimination of a leaving group and a proton.
- In any case, alkyl fluorides would not form the most stable carbocation intermediate because the fluorine atom is such a strong electron-withdrawing group that it destabilizes positive charges on adjacent carbon atoms.