B hsch 2 ch 2 br naoh s c brch 2 ch 2 ch 2 ch 2 br

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Using the rate law for such reaction, explain why (N = nucleophile; L = leaving group). b. HSCH 2 CH 2 Br + NaOH S c. BrCH 2 CH 2 CH 2 CH 2 Br + excess NH 3 H N Provide the intimate mechanistic details of the following intramolecular reactions ( i.e. all elementary chemical steps including proton movement). Remember that acid-base reactions are one of the fastest chemical reactions that you know about, far faster than any SN2 process. In the term of one your peers, proton transfers are wicked fast! intramolecular cyclization: N intermolecular cyclization: L L N N N N L N Chem 33, Kanan & Stack, 2012, PS 7; pg 3
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5. Consider the following reactions in which two distinct pathways lead to two different products. S CH 3 + NC S CH 3 S + major product minor product CN a. The mechanistic pathway to the major product is (circle): b. The mechanistic pathway to the minor product is (circle): S N 1 S N 2 d. If the product ratio is 100:1 (major:minor), complete the reaction coordinate diagram to reflect this product distribution . CH 3 CN DMF S N 1 S N 2 c. At 300 K, the free energy of the reaction to the major and minor products are -20 and -10 kcal mol -1 , respectively. Briefly explain this dramatic difference. minor SM reaction coordinate Gibbs energy -20 kcal mol -1 major -10 kcal mol -1 e. If the product ratio is 100:1 at 300 K, this reaction is under the following control (circle): thermodynamic kinetic Chem 33, Kanan & Stack, 2012, PS 7; pg 4
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a. NaSeMe DMF b. CH 3 Br Br H 3 C c. Cl + I - acetone d. O g. f. EtOH NaOH 6. Predict the major product of the following substitution reactions. If no reaction is expected, write NR. In determining whether a reaction goes via an SN1 or SN2 pathway, consider the nature of the substrate (1°, 2°, or 3°) and the nature of the leaving group.
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