Reactions are impacted by various factors that depend on the mechanism of the reaction. Some of the variables for substitution reactions are:           • strength of the nucleophile           • concentration of the nucleophile           • leaving group ability (i.e., is it a “bad” or a “good” leaving group? In an SN2 reaction, the nucleophile forces the leaving group to leave. (This is the rate-determining step of the reaction.) In an SN1 reaction, the nucleophile does not attack until the leaving group has left. (When the leaving group leaves, this is the rate-determining step of the reaction.)     Based on the information provided in this question, which factors would favor an SN2 reaction? Choose one or more: A.a strong nucleophile B.a good leaving group C.a high concentration of nucleophile       Based on the information provided in this question, which factors would favor an SN1 reaction? Choose one or more: A.a strong nucleophile B.a good leaving group C.a high concentration of nucleophile

What is the energy diagram of the following Sn1 reaction.   2-chloro-2-methylpropane + H2O -> 2-methylpropan-2-ol + HCl   write the rate law equation

attack under the given reaction conditions? carbon is most likely to undergo a nucleophilic (A) II is more likely to be attacked because it has a larger partial positive charge. (B) I is more likely to be attacked because it has a larger partial positive charge. ***** (C) II is more likely to be attacked because it has less steric hindrance. (A) (D) I is more likely to be attacked because it has less steric hindrance. 47. Which alkene will generate the product of this reaction sequence? (C) ? 1. 1) CH₂CH₂MgBr 2) H O R O H 2.00 CN OH (B) (D) K 48. Which are possible enol tautomers of 7-methyl-3-pentanone? HO Et 겨 Et racemic OH H CN OH

For each case below, explain why those are the favored mechanisms Strong bulky bases (primary and secondary) E2 favored over Sy2 Small strong bases/nucleophiles (primary and secondary) - SN2 and E2 Small strong bases/nucleophiles (tertiary) - E2

The hydrolysis of tert-butyl chloride proceeds less rapidly in a solvent mixture which is 15% water/85% acetone than in one which is 85% water/15% acetone. Why? O The reaction proceeds by an SN2 mechanism wherein the rate is increased by increasing the concentration of the nucleophile water. The solvent which contains a greater percentage of water is less polar, and this destabilizes the tert-butyl chloride. O None of the above. O The reaction proceeds by an SN1 mechanism wherein the rate is increased by increasing the concentration of the nucleophile water. O The transition state in the carbocation formation step is better stabilized in the more polar solvent mixture.

For each pair of compounds determine which will undergo electrophilic substitution faster. (d) NO2 (9) SCH, (e) OH (h) HO

Draw out the most likely propagation step of these reactions of radicals with hydrocarbons based upon radical stability of the product radical. Then, propose a termination step that would make a likely stable (non-radical) product of the reaction. b) -Br

3. Identify the dominant mechanism(s) (Sn1, Sn2, E1, E2) that occurs in each reaction and fill in the boxes with the missing reagent or product. (Hint: Identify the type of nucleophile/base and electrophile you're dealing with to help narrow your options.) Mechanism Starting Material Reagent Major Organic Product(s) КОСН-СН, Br LİNHCH2CH3 NaNH2 H Br

18. a. Label the reactive features, highlight the most reactive one, then highlight what it needs. Also, state if the reaction will start to create a carbocation, carbon radical, or carbanion, or will cause loss of aromatic character. If a carbocation, carbon radical, or carbanion starts to develop, label where that will occur. 3-bromo-3-methylhexane + potassium hydroxide in THF b. Use mechanism arrows to illustrate the reaction that occurs. c. If applicable, use stabilization resources to deal with the carbocation, carbon radical, or carbanion that starts to develop during the reaction, and draw the structure of any resonance-stabilized intermediate. d. Continue labeling and diagramming the reaction until you find the major stable product(s). e. Finally, state the stereochemistry of the major product(s) and use either Fisher projection or perspective formula representations to illustrate that stereochemistry.