Pham Chem 14D Fall 2023 Problem Set 3 I General Knowledge Problem Set 3 Below are common mistakes when planning out a synthesis mechanism Briefly state using 10 words or fewer what is wrong with each of the scenarios below a b c Ethambutol Naproxen Your choice d Stereochemistry may only be a concept in our organic chemistry classes but in organic synthesis the importance of creating and or isolating the correct stereoisomer can be crucial Look up the following two drugs and a molecule of your own and fill in the table below Name Structure What is the What is the enantiomer used for enantiomer used for or what does it do or what does it do Pham Chem 14D Fall 2023 Problem Set 3 II Reaction Check Alkenes For each of the following alkene reactions draw the major product and indicate the correct regiochemical and stereochemical outcomes by circling the correct answer in each column You do not need to draw dashes and wedges in the product structure since you are specifying how the addition occurs in the last column Given reactants Draw the product Regiochemistry Relative Addition circle one Markovnikov circle one Syn addition Anti Markovnikov Anti addition N A Mixed Both Markovnikov Syn addition Anti Markovnikov Anti addition N A Mixed Both Markovnikov Syn addition Anti Markovnikov Anti addition N A Mixed Both Markovnikov Syn addition Anti Markovnikov Markovnikov Syn addition Anti Markovnikov Anti addition Mixed Both Anti addition Mixed Both N A N A Markovnikov Syn addition Anti Markovnikov Anti addition N A Mixed Both Pham Chem 14D Fall 2023 Problem Set 3 III Mechanisms Provide a complete arrow pushing mechanism for the following reactions in the boxes provided Show every step clearly and separately including intermediates and formal charges Messiness may result in lost points Note Other products may also be formed in small quantities but you only have to show the mechanism to form the product shown a b Pham Chem 14D Fall 2023 Problem Set 3 IV Reactions Complete the following reactions by drawing clear structures for the major organic product reagent or reactant Remember stereochemistry where applicable Notes on inputting answers in boxes If the answer is a single compound give its structure clearly If the answer is a racemic mixture you may give one enantiomer s structure clearly and write racemic or under the answer If the answer is a mixture of diastereomers you must clearly give the individual structure of each product c Note DBE Double bond equivalence the of pi bonds rings in a molecule a b d Pham Chem 14D Fall 2023 Problem Set 3 V Synthesis Show how the following multi step chemical transformation can take place Provide reagents for each step in the synthesis Include structures of intermediate products that could be isolated after each step Do not provide a mechanism or curved arrows Be clear Messiness may result in lost points Note You are usually allowed to start with more than one molecule of the starting material in this case 1 bromo 2 2 dimethylpropane e