d) If the reaction is carried out at 0°C, what would be the major product? c) The reaction is then carried out at 80°C, and the major product was found to be the same as when the reaction was carried out at 0°C. What is the kinetic product and what is the thermodynamic product? f) Assuming the first step is rate determining, and the reaction is spontaneous, sketch a reaction coordinate (energy diagram) for the mechanism drawn in part c). Label the reactants, products (kinetic and thermodynamic), intermediates, transition states, energy of activation, and energy of reaction. AG Reaction Coordinate

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
Section: Chapter Questions
Problem 31CTQ
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Please do parts D, E, and F

6. Consider the following reaction:
CH3
HBr.
?
ČH3
a) Draw the two possible allylic cations that could be produced as an intermediate in this addition
reaction; include resonance structures.
b) Which of these allylic cations is more stable, explain briefly how you arrived at that conclusion?
c) Draw the complete mechanism for the addition reaction involving the more stable allylic cation
intermediate showing the formation of both the 1,2 and 1,4 addition products, include arrows, formal
charges and electron pairs.
d) If the reaction is carried out at 0°C, what would be the major product?
e) The reaction is then carried out at 80°C, and the major product was found to be the same as when the
reaction was carried out at 0°C. What is the kinetic product and what is the thermodynamic product?
f) Assuming the first step is rate determining, and the reaction is spontaneous, sketch a reaction
coordinate (energy diagram) for the mechanism drawn in part c). Label the reactants, products (kinetic
and thermodynamic), intermediates, transition states, energy of activation, and energy of reaction.
ΔG
Reaction Coordinate
Transcribed Image Text:6. Consider the following reaction: CH3 HBr. ? ČH3 a) Draw the two possible allylic cations that could be produced as an intermediate in this addition reaction; include resonance structures. b) Which of these allylic cations is more stable, explain briefly how you arrived at that conclusion? c) Draw the complete mechanism for the addition reaction involving the more stable allylic cation intermediate showing the formation of both the 1,2 and 1,4 addition products, include arrows, formal charges and electron pairs. d) If the reaction is carried out at 0°C, what would be the major product? e) The reaction is then carried out at 80°C, and the major product was found to be the same as when the reaction was carried out at 0°C. What is the kinetic product and what is the thermodynamic product? f) Assuming the first step is rate determining, and the reaction is spontaneous, sketch a reaction coordinate (energy diagram) for the mechanism drawn in part c). Label the reactants, products (kinetic and thermodynamic), intermediates, transition states, energy of activation, and energy of reaction. ΔG Reaction Coordinate
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