6. Provide the product of the following series of reactions. Provide a mechanism which accounts for the formation of the product. (Note: There is no quench after step 1. That is, the alkyl halide in step 2 is added immediately.) 1. میں & 2. then add CI

5. Synthesis a) Show how to make the following ether starting from Propylchloride and 2-lodopropane, keep in mind that secondary alkyl halides eliminate with nucleophiles that are strong bases to give you the alkene products. CI

1. Provide the mechanism for the following reaction. OH H2SO4 HeAt CH2 CH3 CH3

Show an example of this mechanism using this general reaction.

4. Propose an efficient synthetic route (along with intermediates) for the following transformation. Note: Use cyclohexane as the starting point for both cyclohexyl rings in the product.

Q4. Alkyl halides are good at doing substitution (SN2/SN1) and elimination (E1/E2) reactions because the halide (X-) is a good LG. Alcohols on the other hand are not suitable for these reactions since hydroxide (¯OH) is a poor LG. However, an OH can be converted into a OTs (tosyl group) by reacting an alcohol with TsCl in presence of a base. An OTs is a good LG, and this allows us to indirectly (via OTs) use alcohols in substitution (SN2/SN1) and elimination (E1/E2) reactions. (4) OH TsCl NEt3 OTS Tosyl ester NaCN DMSO + HNEt3 Determine the major/minor products CH3OH heat OTS Tosyl ester TsCl = NaOCH3 CH3OH DBU Ś=0 CI

5. Provide the product that will result for the following reaction and provide the complete mechanism. CH,N2 НО 오

Rank the following compounds in order of increasing acidity

3. Perform the following tasks for each reaction. i. Identify the functional group (FG) in the starting material with the most accurate name: alcohol, aldehyde, epoxide, ester, ether, or halohydrin. ii. Label the reagent over the arrow as a good nucleophile; a strong base; and/or a strong acid. (A reagent can have more than one label.) Draw the major organic product. (Hint: Remember to keep track of stereochemistry over the course of the reaction if given. It may be helpful to redraw the starting material in the conformation needed to close epoxide ring.) ii. iii. Product i. Starting Material OH ii. Reagent a. D. NaOH FG = b. Excess HBr FG = с. 1. Li(CH2);CH3 2. H3O* (Acidic workup for neutralizing charge) FG = d. ОН NaH FG = е. HBr FG =

Don’t understand 7