CH241 Practice Final Exam Question 1 a Circle the strongest base from the list below O OCH3 F NH4 b Circle the strongest acid from the list below H O HF O NH4 H3C H H3C OH c Circle the strongest nucleophile from the list below acetate ammonia methanol fluoride d Circle the most stable carbocation from the list below OCH3 Question 4 3 points Addition of HCl to propyne gives which of the following dichlorides Cl Cl Cl Cl Cl Cl Cl Cl Question 2 a Circle meso 2 3 dichlorobutane Cl Cl Cl Cl Cl Cl Cl Cl b Draw the compound that you circled in part a as a Newman projection you may use the template if you wish c Circle a diastereomer of E 2 chloro 2 butene Cl Cl Cl Cl d Draw a structural isomer of E 2 chloro 2 butene that is chiral e Circle the compound below that contains a bridged bicyclic ring system Question 3 a You have a sample of known chiral compound If the optical rotation of the enantiomer is reported at 60 0 and your sample has an optical rotation of 30 0 what percent of your sample is the enantiomer b Draw cis 1 3 dimethylcyclohexane in it s lowest energy chair conformation c Clearly explain why bromocyclopropane does not undergo an SN1 reaction if you wish you can compare it to 2 bromopropane which does undergo an SN1 reaction Question 4 Provide clear structural drawings for the following compounds tosyl chloride borane an amide an ester diethyl ether tert butanol Question 5 Provide the missing reagents and products to complete the reactions shown below O H a H H O CH3 CH3 H3C b H CH3 H2 Pd C c CH3 d Br CH3 H3C Br Question 6 Provide the missing starting materials reagents and products to complete the reactions shown below OH OH CH3 CH3 a H OH b 2 SMe2 Br excess NaSCH3 c H Br 1 butene h d O 1 O3 H2C N2 H3C O H Question 7 Provide the missing reagents and products to complete the reactions shown below Me a Me C C H HBr C H C5H9Br MgBr b OH O c 1 excess conc HBr 2 ethylamine C7H15N Question 8 Epoxides can be synthesized by treating an alcohol containing a proximal halogen atom with strong base as shown below HO KOtBu O KBr HOtBu Br a Provide a mechanism for the reaction above b Explain why trans 2 chlorocyclohexanol will form an epoxide when treated with strong base but cis 2 chlorocyclohexanol will not Hint Drawing the starting materials in their chair forms will aid your analysis OH KOtBu O Cl OH KOtBu O Cl Not Formed Question 9 Provide a mechanism for the following reaction OCH3 Br H3C AgNO3 H3CO MeOH H3C OCH3