Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 6, Problem 48P

Open the computer molecular model tided “1-Bromo[2.2.1]bicycloheptane LUMO” at WileyPLUS for the lowest unoccupied molecular orbital (LUMO) of this compound. Where is the lobe of the LUMO with which the HOMO of a nucleophile would interact in an S N 2 reaction?

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3) Any compound or ion with at least one lone pair can be considered a base and/or a nucleophile. The relative basicity and nucleophilicity of the species is one of the most important factors that determine the mechanism of a reaction on sp³-carbon atoms. Please show an example of a) a reagent that is a strong nucleophile and a strong base, b) a reagent that is a weak nucleophile and a strong base, c) a reagent that is a strong nucleophile and a weak base, d) a reagent that is a weak nucleophile and a weak base. Which nitrogen atom in the structure below is most nucleophilic? Please explain by discussing the electron density around each nitrogen atom. Show at least three resonance structures of the compound. N.
In the given condensed formula, I understand that there will be a carbocation rearrangement due to excess hydrogen and an E1 mechanism, however, I have trouble in understanding where this bond between the nucleophile and electrophile is formed.
HW 10 #22  I need help in the last part
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