Self Assessment Test 1. a) (10 pts) Identify the arrowed functional groups in the following compounds : NOOOHOHCOMPOUND BOOOHOCOMPOUND ANH2BrF b) (2 pts) How many sp2 hybridized carbon atoms are present in Compound A? : c) (2 pts) How many sp3 hybridized carbon atoms are present in Compound B? : d) (3 pts) What is the molecular formula of Compound A?2. (6 pts) For each of the following compounds draw one additional resonance form indicating the movement of electrons with curved arrows on the structure in the box. Indicate also all lone pairs of electrons and charges. Based on the movement of electrons indicated by the curved arrows, draw the resulting resonance structure. Show all lone pairs of electrons and charges where appropriate.3. (8 pts) a) Draw the structures of two constitutional isomers of cyclic alcohols with molecular formula C6H12O b) Draw the structures of two stereoisomers of cyclic halides with formula C9H17Br 4. (4 pts) Indicate the formal charges for the arrowed atoms. Show calculations for full credit. 5. (6 pts) Classify each of the reactions below as elimination (E), rearrangement (R), substitution (S) or addition (A). OCH2CH3OOHOCH2CH2OHOCH2CH3OOOacid catalystacid catalystSO3H2SO4CH3CH3SO3H6. (6 pts) Draw an energy diagram profile for a three step endergonic reaction with a high energy of activation for the second step and lower energy of activation for the other steps. Label the axes of the diagram and any transition states (TS1, TS2, etc) and intermediates ( I1, I2, etc). 7. (4 pts) Which of the alkenes below is the least stable? Which is the lowest in energy? 8. (a) (4pts) Place a star (*) next to each chirality center present in the following structures. (b) (2pts) Enter in the boxes the maximum number of stereoisomers expected.9. (8 pts) Label each pair of structures below as constitutional isomer (C), diastereomer (D), enantiomers (E), identical (I), meso (M) or none of the above (N). 10. (6 pts) Complete the following chart. (Choose your answers from the menu). ReactionRegiochemistryStereochemistryHydroboration of alkenes followed by H2O2,OH-Acid catalyzed addition of waterOsO4followed by NaHSO3and H2O A : Syn B : Non-Markovnikov C : Anti D : Markovnikov E : Not applicable11. (6 pts) Identify the mechanism by which each of the following reactions proceeds from among the mechanisms listed. Use the letters a - i for your answers. a = Proton transfer d = Radical chain addition g = E2 Elimination b = Lewis acid/base e = Electrophilic addition h = SN1 Nucleophilic substitution c = Radical chain substitution f = E1 Elimination i = SN2 Nucleophilic substitution i) ii) Reaction i) : __________ Reaction ii) : ___________ 12. (3 pts) The two reactants shown below are combined to bring about a nucleophilic substitution reaction. OTosF12345CN67 f) HCN g) CH3+ h) -OTos i) CH3- j) HBr k) CN- l) F+ m) none Which number designates the electrophilic atom at which substitution occurs? : Which letter corresponds to the leaving group? : Which letter designates the nucleophile? :13. (6 pts) Consider the following structure to answer the following questions: a) circle THE MOST acidic hydrogen atom b) square THE SECOND MOST acidic hydrogen atom c) draw a triangle around THE LEAST acidic hydrogen atom 14. (4 pts) 9. Draw the products resulting from the electron flow indicated by the curved arrows. BrHBr 15. (3 pts) Circle the MOST stable carbocation and square the LEAST stable: 16. (3 pts) Draw the structure of (3R,4R)-4-chloro-1,1,3-trimethylcyclopentane. (4 pts) Draw the two chair conformations of trans-1-(tert-butyl)-3-fluorocyclohexane; circle the structure with the tert-butyl in equatorial