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- Draw the major organic substitution product or products for (2R,3S)-2-bromo-3-methylpentane reacting with the given nucleophile. Clearly drawn the stereochemistry, including a wedged bond, a dashed bond and two in-plane bonds at each stereogenic center. Omit any byproducts. Br CH;CH20 (conc.) H.rank these from least to most reactive in nucleophilic acyl substitution with a nucleophile I)CH3COOC2H5 II) CH3COO-Na+ III)CH3COCl IV) CH3CONH2b) Explain in detail what characteristics of the alkyl halide influence whether a mechanism will be SN1 or SN2. c) Explain in detail what characteristics of a nucleophile influence whether a reaction will be SN1 or SN2.
- The following molecules are subject to substitution (SN1 or SN2) reaction conditions. a) Identify if the leaving group (-Br) is attached to a 3°, 2°, 1°, or methyl Carbon. b) Rank the molecule with respect to their SN1 reactivity, with 1 being the fastest and 4 being the slowest. c) Rank the molecule with respect to their SN2 reactivity, with 1 being the fastest and 4 being the slowest. Br Br CH3B Br a. type of Carbon on C-Br b. SN1 reactivity (1 fastest, 4 slowest) c. SN2 reactivity (1 fastest, 4 slowest)Each of the following may participate in an elimination reaction, under the proper conditions. (a) Circle the alpha (a) carbon. (b) Circle the beta (B) carbon(s). (c) Draw the alkene product(s) that may form, with the new double bond between the a and ß positions. (d) If more than one alkene product is possible, circle the most stable (Zaitsev) product. A В J C K E F G 33-0Organic Chemistry - nucleophilic substitution and elimination rxns chapter
- What is the strongest nucleophile, NH3, CH4, CH3O-, or H2O?5. Predict whether each reaction will occur via SN2 or E2 mechanism and draw the product. Write 'NR' if the reaction will not proceed as written. & CH3CI NaCl Acetone KOt-Bu t-BuOH KOt-Bu t-BuOH NaOEt EtOH• Same reagents as acid-catalyzed dehydration, except starting with a instead of an alcohol. • Same as the general mechanism hydrohalogenation, except with . Remember that EVERY acid-cat. mechanism begins with General Reaction: EXAMPLE: Provide H₂O H₂SO4 EXAMPLE: Provide the mechanism for the following addition reaction. H₂O H₂SO4 OH WH H₂O H₂SO4 as the nucleophile and ends with do PRACTICE: Provide the mechanism and predict the product of the following reaction. MAXO
- (i) In SN2 reactions involving anionic nucleophiles, the rate is greater when the counterion is Cs* rather than Lit. Also, the rate of SN2 reactions of anionic nucleophiles with Li* counterion is greatly increased on addition of compound A. Explain these results. AFor each alkyl halide and nucleophile: [1] Draw the product of nucleophilic substitution; [2] determine the likely mechanism (Sn1 or Sn2) for each reaction.2. Draw the structures and explain why CH3CH₂O and CH3CO₂ are good nucleophiles but CH3SO3, water, and alcohols (R-OH) are poor nucleophiles. Propose a 'cutoff' for the amount of negative charge needed to be a good nucleophile. CH3CH₂O CH3CO₂ CH3SO3 H₂O CH₂OH