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Nucleophilic addition tends to be irreversible if the negative charge that develops in the adduct is significantly better stabilized than it is in the nucleophile. This occurs in the nucleophile that has the negative charge located on a carbon or hydrogen atom, and the negative charge is not stabilized by resonance or inductive effects. Therefore, nucleophilic addition to a carbonyl carbon tends to be irreversible when it involves a very strong
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Organic Chemistry: Principles and Mechanisms (Second Edition)
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- Explain the different products of the following two reactions by considering the mechanism by which each reaction proceeds. As part of your explanation, use the curved arrow formalism to draw a mechanism for each reaction. CH,OH CH2=CH-CH-CH, + Na*¯OCH, CH;=CH-CH-CH3 Br OCH, CH,=CH-CH-CH, + CH,OH – CH,=CH–CH–CH, + CH,CH=CHCH, Br OCH, OCH,arrow_forwardDraw the mechanism for the reaction of an alkyl halide with sodium azide followed by reduction. Complete the mechanism of the initial step of the reaction, then identify the key intermediate and the product. Step 1: Draw curved arrows. o z + Na + || : z: I Step 2: Complete the intermediate. Na +arrow_forwardo Predict the two major organic products of the reaction. (HI behaves as an HX reagent.) H₂C ΤΟ + CH3 H—I CH3 Draw the two major organic products. H₂C H H CH₂ CH₂arrow_forward
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