3. For the following reaction: NaOH DMSO ? a. identify the type of alkyl halide: b. identify the type of nucleophile/base: c. predict the anticipated mechanism(s): d. predict the major organic product by drawing the appropriate mechanism:

1. .CI HC C: Li HC CH LICI 2. -CH3 OH Aqueous HO-S- -CH3 acetone g = SN1 Nucleophilic substitution Electrophilic a = Proton transfer addition h = SN2 Nucleophilic substitution b = Lewis acid/base e = El Elimination c = Radical chain f= E2 Elimination substitution Identify the mechanism by which each of the reactions above proceeds from the mechanisms listed. Use the letters a - i for your answers. among 1. 2.

Draw the full electron pushing mechanism for the reaction depicted including ALL intermediates (with lone pairs and formal charges). Clearly label the electrophile and nucleophile in each step where appropriate.

Name: Recitation Worksheet 4 1) Propose a plausible mechanism for the following reactions: a. (For this mechanism, also determine the reagent used.) b. O O ? HO HCI (xs) Section: A OH 2 eq. CI

Synthesize the following compound from cyclohexanol using any other organic or inorganic compounds. HO. Part 1 out of 2 Preparation of the Grignard reagent: Book rint rences OH draw structure ... draw structure... Draw the intermediate product formed above and select the correct reagent A. O MgBr, O CH;Br O Brz PB13 Draw the intermediate product formed above and select the correct reagent B. O MgBr O Mgo O O Mgl, O Mg Hint Prev 3 of .8 Next > re to search

Draw the major organic product for each of the hydroboration-oxidation reactions. Disregard stereochemistry. Draw the product of Reaction A. Select Draw Rings More ||||||CH|OB Reaction A. 1. B₂H6 2. H₂O₂ (aq) 3M NaOH Reaction B. 1. B₂H6 2. H₂O₂ (aq) 3M NaOH S 3 Draw the product in reaction B. Select Draw Rings More |||||||||CH|OB Erase Q2Q Erase Q2Q

3. Draw the reaction mechanism for the following reactions. When possible, label nucleophiles/electrophiles, carbocations, and oxonium ions. H* CI. a) H. + H2O + НОCHЗ H* OH H* H;C

1. Give the major product(s) of the following reactions as needed. Include any stereoisomers. NaOEt 1. Br NaOH Br 2. NaOtBu 3. A MEOH 4. Br 2. Which reaction will proceed faster A or B? H,S H2S "CI .... в

Which is the MAJOR product of the following reaction? Et 1) BH3:THF 2) H2O2, NaOH Which of the following best describes a key step in the mechanism for the reaction below? HO ... CH3 -CH3 dihydroxylation + en H3C- H3C- HO. electrophilic addition reaction to form a carbocation intermediate B nucleophilic attack by an alkene to form a cyclic (epoxide) intermediate elimination reaction by abstraction of a beta-hydrogen D free-radical substitution at the carbonyl carbon Which alkene will produce the HIGHEST yield of the alkyl halide below? Br. alkene HBr |

027 In Part 1 add the curved arrows to the nucleophilic acyl substitution reaction mechanism. In Part 2, answer the multiple-choice question about the reaction in Part 1. Part 1 4 See Periodic Table O See Hint :0: :Br: Add the missing curved arrow notation. S CI Br Part 2 Which statement is most correct regarding the equilibrium for the above reaction? Choose one: O The equilibrium favors the right (i.e., Kea > 1) because acetate is a better leaving group than bromide. O The equilibrium favors the right (i.e., Kea > 1) because bromide is a better leaving group than acetate. O The equilibrium favors the left (i.e., Keq« 1) because acetate is a better leaving group than bromide. O The equilibrium favors the left (i.e., Keg 1) because bromide is a better leaving group than acetate. +