1. What product is expected to form in an SN2reaction of OH with (R)-2-bromobutane? Show the stereochemistry of the reactant and the product. 2. What product is expected to form from the SN2reaction of 1-bromopentane with а. КОН? B. Nal? 3. What product would you expect to obtain from a nucleophilic substitution reaction of (S)-2- bromohexane with CH3CO? Assume that inversion configuration occurs, and show the stereochemistry of both reactant and product?

Electrophilic bromination of an equimolar mixture of methylbenzene (toluene) and (trifluoromethyl)benzene with one equivalent of bromine (in the presence of FeBr3) gives exclusively 1-bromo-2-methylbenzene and 1-bromo-4-methylbenzene. a. Explain why none of the (trifluoromethyl)benzene reacts b. Explain the regiochemical outcome of the reaction In other words, why are 1-bromo-2-methylbenzene and 1-bromo-4-methylbenzene formed from the toluene?

Draw the structure(s) of the major organic product(s) of the following reaction. 1. KH / THF 20° C 2. 1 eq. H₂C=CH-Br You do not have to consider stereochemistry. • Omit products derived from the acidic or basic reagent itself, e.g. HN(i-Pr)₂ derived from N(i-Pr)₂- If no reaction occurs, draw the organic starting material. If substantial starting material is present at the end of the reaction, include it in the products. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. 90-85

Which one of these provides the strongest nucleophile in an SN2 reaction? a) HC=N b) NaC-N c) NH3 d) NH4 O b P. C. a.