DISCLAIMER DISCLAIMER The questions within this document were asked on in person exams in the past two academic years and cover topics from Wade s chapters 4 6 The questions within this document is more than one exam s worth of questions These questions are provided for you to get a feel for some types of questions that may be asked and the difficulty level in which questions are asked This is NOT given to show the exact format or length of the exam The exam given this year will have some similarities but will NOT follow the exact format of these questions These questions are also NOT all inclusive All the material you are responsible for may not have been covered within these questions Make sure you are reviewing chapters 4 6 of our textbook to make sure you are covering all appropriate material An answer key will be provided as a courtesy on Monday October 23 it is your responsibility to check the answer key for accuracy There may or may not be some typographical errors both in the exam itself or the key These questions will be most useful to you if you wait until you have studied for the exam and do not use your notes or any other materials 1 Former Exam Questions Topics from Wade chapters 1 5 1 Circle the correct response a Which of the following statements about the equilibrium constant Keq is true A When Keq 1 the equilibrium favors the reactants B When Keq 1 the equilibrium favors the products C The size of Keq tells about the position of equilibrium D For a reaction to be useful the equilibrium must favor the reactants b What is the enantiomeric excess of a mixture that has 70 R enantiomer and 30 S enantiomer A 30 B 40 C 70 D 85 c Which of the following is an example of a meso compound d Which of the following molecules can rotate polarized light e How many transition states are present in the reaction in the energy diagram A 0 B 1 C 2 D 3 f Which of the following represents a meso compound Page of 8 2 ClClBrOH Former Exam Questions Topics from Wade chapters 1 5 g The optical rotation measured for a racemic mixture of a compound is 0 because A the molecules in a racemic mixture do not rotate plane polarized light B enantiomers rotate plane polarized light equally but in opposite directions C the electric and magnetic fields of plane polarized light are orthogonal D the electric and magnetic fields of plane polarized light are rotated in opposite directions h Which of the following alkyl halides will have the fastest rate in a solvolysis reaction i Circle the protic solvent j Which of the following nucleophiles is best in acetone CH3COCH3 Cl Br I CH3OH k Which of the following conditions would increase the rate of the given reaction A Change the solvent to dimethyl sulfoxide DMSO B Change the solvent to methanol C Increase the concentration of the nucleophile D Increase the concentration of the tert butyl chloride Page of 8 3 Former Exam Questions Topics from Wade chapters 1 5 l Which of the following molecules could be used to separate a mixture of enantiomers m Considering the SN1 and SN2 mechanisms the energy diagram shown below corresponds to n Which of the following undergoes a substitution reaction with sodium cyanide in DMSO at the faster rate A only SN1 C only SN2 A CH3CH2F C CH3CH2Br o Which of the following is chiral B both SN1 and SN2 B CH3CH2Cl D CH3CH2I Page of 8 4 OHOHOOHOHOHOOH Former Exam Questions Topics from Wade chapters 1 5 p Which of the following statements is FALSE A The terms asymmetric center and stereocenter mean the same thing B A molecule with asymmetric centers can be chiral C A molecule with asymmetric centers can be achiral D A molecule without asymmetric centers can be chiral E A molecule without asymmetric centers can be achiral q Which of the following alkanes will produce only one monochlorinated product during the reaction with chlorine and heat 2 What is the relationship between each pair of compounds Choose from enantiomers diastereomers constitutional isomers or identical 3 The specific rotation of a mixture containing a 9 1 ratio of R and S enantiomers of a compound is found to be 40 What is the specific rotation of the S enantiomer Page of 8 5 Former Exam Questions Topics from Wade chapters 1 5 4 For the following molecules a Determine the R or S configuration of the three labeled carbon atoms Write your answer in the box 6 pts 2 pts each b For each set of compounds determine if they are constitutional isomers enantiomers identical compounds or diastereomers Write your answer on the line 4 pts 2 pts each i ii 5 Circle all stereocenters in the following compound 5 pts Page of 8 6 HOBrClRelationship HOClBr Former Exam Questions Topics from Wade chapters 1 5 6 For the following molecules label the configuration of the asymmetric carbons as either R or S Write your answer in the indicated boxes 9 pts 3 pts each 7 Free radical bromination of the following alkane can result in two monobrominated products i Draw the structures of both products in the provided boxes ii If the relative rate of bromination for tertiary hydrogens is 1500 times faster than that of the primary hydrogens determine the expected molar ratio between the two products 8 Write the mechanism for the radical reaction below Be sure to label the steps as either initiation propagation or termination Only one termination step needs to be shown 6 pts Page of 8 7 Former Exam Questions Topics from Wade chapters 1 5 9 Substitution For the following reactions i Indicate if the mechanism goes by SN2 or SN1 ii Predict the major organic product or products for each mechanism type iii Be sure to show stereochemistry where applicable If a racemate forms draw one isomer and write ent Page of 8 8