C they react at the same rate nitrogen mustards later

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c) they react at the same rate ( Nitrogen mustards later found use as “weapons” against cancer ) Why is the sulfur mustard hydrolysis faster? H 2 O H 2 O HCl 13 + HCl + HCl What type of reaction is this? a) S N 1 b) S N 2 c) E1 d) E2
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12/10/2010 3 Which atom is the leaving group? H 2 O a b c d e 14 + HCl Which atom is the best nucleophile? + HCl H 2 O 15 Sulfur reacts faster than water: better nucleophile intramolecular reaction Using the curved arrow formalism, draw a mechanism for the formation of the product. H 2 O + HCl 16 Sulfur reacts faster than water: better nucleophile intramolecular reaction H 2 O + HCl 17 Sulfur reacts a second time: 2 moles of HCl from 1 mole of mustard slow fast H 2 O + HCl 18 fast The overall reaction rate will be a) zero order in [H 2 O] b) first order in [H 2 O] c) second order in [H 2 O] Δ G The first step is rate-determining 19 E R
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12/10/2010 4 Predict the product of hydrolysis. Which structure is the correct intermediate? 20 A B Predict the product of hydrolysis. 21 A B C D Poison Gas and Chemotherapy Alkylated DNA Cross-linked DNA Mustard Gas Cytoxan Chemotherapeutic agent 22 What will the exam look like? (preliminary) Tools for understanding, remembering, and predicting reactions.
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