Answered: 7. Which of the following violates the…

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7. Which of the following violates the rules for curved arrows (when drawing esonance structures)?

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter17: Conjugation And Molecular Orbital (mo) Theory

Section: Chapter Questions

Problem 6E

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Spectroanalytical Methods

Spectroanalytical methods measure the wavelength and intensity of radiations that are either emitted or absorbed by a molecular or atomic species. These methods are useful for evaluating the electronic or atomic arrangement of the molecules of a given analyte.

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7.
Which of the following violates the rules for curved arrows (when drawing
esonance structures)?

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6. Breaking peptide bonds is hard. a) Draw steps for (i) addition of water and (ii) elimination of the amine from the CO-NH bond of R-CO-NH-R' ("the reactant"). Include any intermediate steps like proton transfer. b) Draw a resonance structure for the reactant. c) What is the hybridization of the reactant's indicated (i) C, (ii) N, and (iii) O? d) What 2 factors make this hydrolysis reaction slower than hydrolysis of R-co-S-R'-? e) In nature, peptide bonds are hydrolyzed by enzymes including cysteine proteases. Cysteine's structure is HS HO ÑH2 Draw nucleophilic attack of cysteine's thiol on the reactant with the arrow formalism. f) In the resulting tetrahedral intermediate, what is the best leaving group? g) Show how an acidic residue of an enzyme (which you can draw as HA) might help facilitate departure of the amine as the leaving group, by drawing a suitable reaction mechanism (including the acid proton) using the arrow formalism.