Question

(6 pts) The following molecule (isochorismate) can potentially undergo two different pericyclic reactions, a [4+2] cycloaddition or a [1,5] sigmatropic shift. (a) Draw arrow pushing for the [4+2] cycloaddition. Is this cycloaddition normal or inverse electron-demand? (b) Draw arrow pushing for the 1,5 shift. (c) Draw the FMO analysis for the [1,5] shift. (d) Which pericyclic reaction do you think is going to occur? Draw the product(s) you expect. Explain why. COOH .OH [4+2] [1,5] COOH Base ONa COONa Isochorismate a) Draw arrow pushing for the [4+2] cycloaddition. You do not need to show product A. Is this cycloaddition normal or inverse electron-demand? b) Draw arrow pushing for the [1,5] shift. c) Draw the FMO analysis for the [1,5] shift. d) Which pericyclic reaction do you think is going to occur? Draw the product(s) you expect. Explain why.

          (6 pts) The following molecule (isochorismate) can potentially undergo two different pericyclic reactions, a [4+2] cycloaddition or a [1,5] sigmatropic shift.
(a) Draw arrow pushing for the [4+2] cycloaddition. Is this cycloaddition normal or inverse electron-demand?
(b) Draw arrow pushing for the 1,5 shift.
(c) Draw the FMO analysis for the [1,5] shift.
(d) Which pericyclic reaction do you think is going to occur? Draw the product(s) you expect. Explain why.

COOH .OH [4+2] [1,5] COOH
Base
ONa
COONa Isochorismate

a) Draw arrow pushing for the [4+2] cycloaddition. You do not need to show product A. Is this cycloaddition normal or inverse electron-demand?
b) Draw arrow pushing for the [1,5] shift.
c) Draw the FMO analysis for the [1,5] shift.
d) Which pericyclic reaction do you think is going to occur? Draw the product(s) you expect. Explain why.

6 pts the following molecule isochorismate can potentially undergo two different pericyclic reactions a 42 cycloaddition or a 15 sigmatropic shift a draw arrow pushing for the 42 cycloadditi 50328

Added by Julia D.

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