Question

For E2 eliminations in 2-phenylethyl systems, the isotope effect and Hammett p value depend on the nucleophile. From the following data, analyze the nature of the E2 transition state. Identify the most El-like and the most Elcb-like system. Explain. Base Z-Ph-CH-CHU-N(CH3)3 Z-Ph-CH=CH2 Z is substituent for Hammett analysis ky/k 2.5 Base HNLi CH3CH2ONa CF3CH ONa (CH3CH2)2N O 3.1 2.7 1.8 1.0 5.5

Answer 1

Bare Bare Z-ph-c Z-ph-cn=ch. 2- Phao cho egen), z-ph-en = ena + + H Bone from the date It is deen that a Воме E2 KNKD Andi periplanes Transition state Organic compond which can from more stasle. consocation me E-l like and organic Conpand where B corben. have more acidic. hydrogen due to presence of electoon, wim dranin o group ant ane Elers like system I like systen Acidicom - F_ hire stable co ve El stable hydrogen de r Erce-type system, carsanion