Pham Chem 14D Fall 2023 Problem Set 1 I Review Functional Groups Bond Line Structures etc Problem Set 1 Draw bond line structures of molecules with the corresponding criteria Note there are various correct answers a C5H10O2 contains aldehyde b C5H10NBr cyclic contains c 4 carbons contains an and ether amine and alkyl halide alkene and an ester d For the disubstituted cyclohexane molecule below draw both chair formations in their respective boxes Below are common mistakes made when using bond line structures Briefly state what is wrong then draw the corrected structure part g only requires an explanation e f g Pham Chem 14D Fall 2023 Problem Set 1 II Review Acid Base Mechanism Chem 14C likely introduced you to mechanisms through a proton transfer acid base reaction Answer the following questions about the reaction below a Draw the structure of the conjugate acid that is formed b Draw curved arrows above to show the mechanism of proton transfer c Draw 2 other major resonance structures for the conjugate base Of the three structures circle the most contributing resonance structure You do not need to draw curved arrows for these III Review General Knowledge Answer the next few questions about hydroxychloroquine brand name Plaquenil an anti malarial that has gained some media attention these past few months Parts a g refer to the structure of hydroxychloroquine shown on the right a Name the 2 circled functional groups FG1 FG2 b What is the hybridization of this nitrogen c What is the absolute configuration R S of this center d The lone pairs of this nitrogen reside in what orbital e How about the lone pairs of this nitrogen they are in which orbital f How many stereoisomers including the one shown does hydroxychloroquine have g A racemic mixture would include the molecule shown and what other molecule Draw it below IV SN2 Mechanism a Predict the product and draw the mechanism under which it is formed Pham Chem 14D Fall 2023 Problem Set 1 Predict whether the following SN2 reactions will occur faster slower or at the same rate as the original reaction above by circling the right answer and provide a brief explanation why fewer than 10 words c e b d Pham Chem 14D Fall 2023 Problem Set 1 V Mechanism a Provide a complete arrow pushing mechanism for the following reaction in the box 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 b Would the product shown be a created as a racemic mixture Circle ONE YES NO For each of the following molecules below state whether the reaction would proceed faster slower or have no change in rate relative to the original molecule above by circling the correct answer c d e VI General Knowledge Answer the next few questions about the reaction coordinate diagram shown below Pham Chem 14D Fall 2023 Problem Set 1 b Which intermediate step is slower aka the rate determining step Explain how you know label Ea activation energy in the diagram above if it helps your explanation c Label the transition states as TS1 and TS2 in the diagram above Why are they so high in energy Please don t just say the TSs are unstable rather explain why they require so much energy input