Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Which of the following allylic carbocations is the most stable?
Options
- ACH ₃- CH = CH - C H - CH ₃
- BAll have the same stability
- CCH ₃- CH = CH - C H ₂
Correct answer
B. All have the same stability
Step-by-step solution
The stability of carbocations increases with the number of electron-donating groups (+I effect) and the number of -hydrogens (hyperconjugation). All the given species are allylic carbocations and are stabilized by resonance. Their relative stabilities can be determined by the degree of the carbon bearing the positive charge: For CH ₃- CH = CH - C H - CH ₃ , the carbocation is secondary ( 2^ ) allylic and has 3 -hydrogens. For CH ₃- CH = CH - C ( CH ₃)₂ , the carbocation is tertiary ( 3^ ) allylic and has 6 -hydroge