Nomenclature Question

Transcription

1 Topic 13: i-licker Slides Beauchamp 1 omenclature Question 2 2 a. 1,2-diamino-5,11-dioxo-6-isopropoxy-7-hydroxy-9-cyanoundec-3E-en-1-one b. 3-cyano-5-hydroxy-6-isopropoxy-7,11-dioxo-10,11-diaminoundec-8E-enal c. 2-amino-5,11-dioxo-6-(2-methylethoxy)-7-hydroxy-9-cyanoundec-3E-enamide d. 2-(2-oxoethyl)-4-hydroxy-5-(1-methylethoxy)-6,10-dioxo-9,10-diaminodec-3E-enenitrile e. o entirely correct answer is provided Q-1:What are the likely reactions ofthe following carbocation? a. addition b. elimination c. rearrangement d. a & b & c e. a & b otes: pp 1-5 :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

2 Topic 13: i-licker Slides Beauchamp 2 Q-2:What are the likely reactionsofthe following carbocation? 3 3 a. addition b. elimination c. rearrangement d. a & b e. resonance otes: pp 1-5 Q-3:What are sites of partial positive polarity? a. 2,3,5 b. 2,4,6 c. 1,3,5 d. 1,2,4,5 e. 1,2,4,6 otes: pp 1-5 :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

3 Topic 13: i-licker Slides Beauchamp 3 Q-4:What is the best orbital to receive electrons in and the best orbital to donate electrons from? σ σ π σ M's of ethanal Potential Energy otes: pp 3 n 1 π σ σ uclear harges n 2 σ donate accept from into a. π π b. n 1 or n 2 π c. σ σ d. σ σ e. σ σ Q5: ow many different products can form in the following reaction (include stereoisomers)? otes: p 5 D l? a. 2 b. 4 c. 6 d. 8 e. 10 :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

4 Topic 13: i-licker Slides Beauchamp 4 Q6: Which of the following are isomers, stereoisomers (diastereomers, enantiomers)? D D D D 4 D l l l l l nly selected answers are provided, not all possible answers. l l l D D D l 8 D isomers (not stereoisomers) diastereomers enantiomers a. (1,7) (1,2) (3,4) b. (4,5) (1,4) (6,7) c. (3,5) (1,7) (1,2) d. (3,7) (2,3) (7,8) e. There is no answer provided with all parts correct. otes: pp 5 :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

5 Topic 13: i-licker Slides Beauchamp 5 Q7: What is a reasonable sequenceofstepsfor a carbonyl reaction in acid? a 3 3 b elimination product 3 addition product 3 3 c 3 3 elimination product 3 addition product d 3 3 elimination product 3 3 addition product elimination products 3 addition product e. one of the above is a reasonable carbonyl reaction sequence in acid. otes: pp 4 :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

6 Topic 13: i-licker Slides Beauchamp 6 Q8: What is a reasonable sequence of steps for a carbonyl reaction in base? a 3 3 b elimination product 3 addition product 3 3 c 3 3 elimination product 3 addition product 3 d 3 addition product 3 3 elimination product 3 elimination products 3 addition product e. one of the above is a reasonable sequence of steps for a carbonyl reaction in base. otes: p 6 :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

7 Topic 13: i-licker Slides Beauchamp 7 Q9: What is the expected order of reactivity with nucleophiles? l a. 5 > 2 > 4 > 1 > 3 b. 3 > 4 > 1 > 5 > c. 5 > 1 > 2 > 4 > 3 d. 3 > 4 > 2 > 1 > 5 otes: pp 7-8 e. The correct answer is not provided. Q10: Which are tautomers of the given structure? A omparison Structure a. only 1 b. only 2 Possible Tautomers c. only 3 d. 1 and 2 otes: p 8 e. 1, 2 and 3 :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

8 Topic 13: i-licker Slides Beauchamp 8 Q11: What are the expected products in the following reaction? 3 1. LiAl 4 2. D 3 + / D 2 D 2 3 D 3 3 D a. only 1 D b. only 2 c. only 3 d. only 4 otes: pp 9-11 e. only 2 and 3 (racemic mixture) :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

9 Topic 13: i-licker Slides Beauchamp 9 Q12: ow do the following reactions compare? 1 Li 5 a 3 Al 3 2. workup 3 B 3 2. workup 2 Li 6 a 3 3 Al 3 2. workup 3 3 B 3 2. workup Li Li Al 3 Al 3 2. workup 2. workup a. All of the reactions work and deliver 1 equivalent of hydride. b. All of the reactions work and reactions 1,2,5 and 6 deliver 1 equivalent of hydride and reactions 3,4,7,8 deliver 2 equivalents of hydride. c. All of the reactions work and reactions 1,2,4,5,6,8 deliver 1 equivalent of hydride and reactions 3 and 7 deliver 2 equivalents of hydride. d. Reactions 1,2,4,5,6 and 8 deliver 1 equivalent of hydride, reaction 3 delivers 2 equivalents of hydride and reaction 7 does not work. e. o answer above is completely correct. otes: p a a B 3 B 3 2. workup 2. workup :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

10 Topic 13: i-licker Slides Beauchamp 10 Q13: What are the expected products in the following reaction? LiAlD / D 3 D D D 2 D 2 a. only 1 b. only 2 c. only 3 d. only 4 otes: p 11 e. The correct answer is not shown Q14: Which PE vs. PR diagram goes with each reaction? Energy Picture 1 Energy Picture 2 Energy Picture 3 B A B A B otes: pp Potential Energy Potential Energy A Potential Energy A A B A B B Progress of Reaction Progress of Reaction Progress of Reaction a. PE/PR diagram 1 = (1,2,3,4) / PE/PR diagram 2 = (5,6) / PE/PR diagram 3 = (7,8) b. PE/PR diagram 1 = (1,2,7,8) / PE/PR diagram 2 = (3,4) / PE/PR diagram 3 = (3,4) c. PE/PR diagram 1 = (1,2,5,6) / PE/PR diagram 2 = (3,4) / PE/PR diagram 3 = (7,8) d. PE/PR diagram 1 = (7,8) / PE/PR diagram 2 = (5,6) / PE/PR diagram 3 = (1,2,3,4) :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

11 Topic 13: i-licker Slides Beauchamp 11 Q15: What is the order of reactivity (1=fastest)? a 2. slow addition of acid R R cyanohydrins a. 3 > 2 > 4 > 1 because of resonance, inductive and steric effects b. 1 > 3 > 2 > 4 because of resonance and inductive effects c. 2 > 4 > 1 > 3 because of steric and inductive effects d. 1 > 3 > 2 > 4 because of steric and resonance effects e. The correct answer is not shown otes: pp Q16: What atom reacts first when laetrile breaks down in acid to form cyanide? d c otes: pp laetrile e b a -X (acid) 2 sugar benzaldehyde hydrogen cyanide :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

12 Topic 13: i-licker Slides Beauchamp 12 Q17: Match the correct reaction conditions with its proper reaction? ar ar workup 3. workup i ii 1. ar workup iii 1. ar workup iv 1. R 2 B / 2 S 4 2 / g +2 2 / Pd quinoline v vi vii 2 / Pd a / 3 a. reaction 1 = viii, reaction 2 = v, reaction 3 = vi, reaction 4 = ii, reaction 5 = i b. reaction 1 = ix, reaction 2 = vi, reaction 3 = v, reaction 4 = ii, reaction 5 = iv c. reaction 1 = vii, reaction 2 = i, reaction 3 = vi, reaction 4 = iv, reaction 5 = iii d. reaction 1 = ix, reaction 2 = ii, reaction 3 = v, reaction 4 = iii, reaction 5 = i viii ix e. The correct answer is not shown otes: p 21 :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

13 Topic 13: i-licker Slides Beauchamp 13 Q18: Identify any mechanisticstepswhere errors occur? otes: p a. steps 3, 7, 9 b. steps 2, 5, 11 c. steps 4, 6, 10 d. All steps are correct e. The correct answer is not shown :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

14 Topic 13: i-licker Slides Beauchamp 14 Q-19 ow many errors are present in the following mechanism? R R Li R Li R Li Li Li Li Li Li Li metal hexane Li Li Li Li Li Li Li Li a. 0-1 b. 2-3 c. 4-5 d. 6-7 e. >7 Q-20 ow many different R- compounds can be made from the following alkanes (in one reaction)? 4 a. 6 b. 7 c. 8 d. 9 e. >9 :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

15 Topic 13: i-licker Slides Beauchamp 15 Q-21 ow many different R- compounds can be made from the following alkenes (in one reaction)? a. 6 b. 7 c. 8 d. 9 e. 10 Q-22 ow many different R- compounds can be made from the following alcohols (in one reaction)? 3 a. 6 b. 7 c. 8 d. 9 e. 10 :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

16 Topic 13: i-licker Slides Beauchamp 16 Q-23: ow many different carbanions can potentially be made from the starting molecules (after an appropriate number of steps)? Include ALL different possibilities. 4 a b c d e. 17 :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

17 Topic 13: i-licker Slides Beauchamp 17 Q-24: ow many bonds represent a reasonable carbonyl (=) disconnection strategy? a. 0 b. 1 c. 3 d. 4 e. 5 Q-25: ow many bonds represent a reasonable epoxide disconnection strategy? a. 0 b. 1 c. 3 d. 4 e. 5 :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

18 Topic 13: i-licker Slides Beauchamp 18 Q-26: ow many bonds represent a reasonable R-X / organolithium coupling strategy? a. 0 b. 1 c. 3 d. 4 e. 5 Q-27: ow many fatal flaw steps (wrong steps) are present in the following reaction sequences? Each arrow represents a different synthetic step. l 2 / hν l 1. Li 2. 2 r Mg 2. r 3 2 pyridine 4 3. workup B / Mg workup 8 9 a. 0-1 b. 2-3 c. 4-5 d. 6-7 e. 8 :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

19 Topic 13: i-licker Slides Beauchamp 19 Q-28: ow many reasonable strategies could be used to make the target molecule (TM)? More than one step can be used. aldehyde + R / Mg ketone + R / Li ester + R / Mg epoxide + R / Mg TM? aldehyde + alkyne ketone + alkyne ester + LiAl 4 epoxide + LiAl 4 S 1 S 2 alkene a. 0-1 b. 2-3 c. 4-5 d. 6-7 e. 8 :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

20 Topic 13: i-licker Slides Beauchamp 20 Q-29: ow many nitriles below could be prepared using a S strategy and RX compounds? 3 a. 0-1 b. 2-3 c. 4-5 d. 6-7 e. 8 Q-30: ow many proton transfers are needed to workup the reaction to the indicated products? R R intermediate from reaction of nitrile + Grignard 2. workup R R a. 3 b. 4 c. 5 d. 6 e. 7 :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

21 Topic 13: i-licker Slides Beauchamp 21 Q-31: ow many errors are in the following mechanism? 3 2 Li workup a. 0 b. 1 c. 2 d. 3 e :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

22 Topic 13: i-licker Slides Beauchamp 22 Q-32: Use the same 1 st step for all reactions = Mg, and same last step = 3 + / 2. nly the 2 nd step (electrophile) is different in each reaction (shown). ow many answers are wrong? Possible Products a. 3 b. 5 c. 7 d. 11 e. not given :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

23 Topic 13: i-licker Slides Beauchamp 23 Q-33: ow many starting combinations could lead to a reasonably good yield of the product shown (within 2 steps)? Product a. 2 b. 3 c. 4 d. 5 e. 6 Q-34: ow many starting combinations could lead to a reasonably good yield of the product shown (within 3 steps)? ne of these. and Product a. 3 b. 4 c. 5 d. 6 e. 7 :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

24 Topic 13: i-licker Slides Beauchamp 24 Q-35: What would be the most straight forward approach to the following target molecule? a b 2 a TM c 3 3 d. All are similar. e. one are workable. Q-35: Which oxygen is most likely to react with thionyl chloride, in the mechanism to form an acid chloride? a b l S l l S 2 l :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

25 Topic 13: i-licker Slides Beauchamp 25 Q-37 ow many of the following combinations will lead to the indicated target molecule within 2 synthetic steps? Target Molecule? a 10 a. 1-2 b. 3-4 c. 5-6 d. 7-8 e Q-38 Starting from the given molecules, which approaches could lead to the target molecule? Starting Molecules: 4, 3 3, 3 2 3, 4 Target Molecule a b c d e. any of the above could work :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

26 Topic 13: i-licker Slides Beauchamp 26 Q-39 ow many of the following molecules could be made using a 3+1+1strategy? Starting Molecules: 4, 3 3, 3 2 3, 4 Target molecules a. 1 b. 2 c. 3 d. 4 e. o correct answer Q-40 ow many of the following molecules could be made using a 2+2+1strategy? Starting Molecules: 4, 3 3, 3 2 3, 4 Target molecules a. 1 b. 2 c. 3 d. 4 e. o correct answer :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

27 Topic 13: i-licker Slides Beauchamp 27 Q-41 ow many of the following molecules could be made using a 3+2strategy? Starting Molecules: 4, 3 3, 3 2 3, 4 Target molecules a. 1 b. 2 c. 3 d. 4 e. o correct answer :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc

28 Topic 13: i-licker Slides Beauchamp 28 Q-42 ow many errors are in the given ketalization mechanism, used to protect aldehydes and ketones? ketone Ts Ts ethylene glycol remove 2 Ts R ketal R a. 2-3 b. 3-4 c. 5-6 d. 7-8 e. 9 :\Documents and Settings\psbeauchamp.WI\My Documents\classes\315\i-clicker questions\topic 13 arbonyl (=) i-licker Slides for pdf.doc