ACS Organic Chemistry II Final Exam Questions and Answers

ACS Organic Chemistry II Final Exam Questions and Answers

17. What is the predicted reaction? 1º alkyl halide with a strong base? weak base? poor nucleophile?: strong base: Sn2 favored but E2 with strong non-nucle- ophilic bases weak base: Sn2 poor nucleophile: no reaction 18. What is the predicted reaction? 2º alkyl halide with a strong base? weak base? poor nucleophile?: strong base: mostly E2 strong non-nucleophilic bases: mostly Sn2 poor nucleophile: Sn1/E2 (slow) in polar, protic solvents 19. What is the predicted reaction? 3º alkyl halide with a strong base? weak base? poor nucleophile?: strong base: E2 strong non-nucleophilic bases: Sn1/E1 in polar protic solvents poor nucleophile: Sn1/E1 in polar, protic solvents 20. What is the configuration of the product in the base-catalyzed hydrolysis of (R)-1- choloro-1-deuteriobutane?: (S)-1-deuterio-1-butanol (Sn2) 21. Where isthe largest molecule on the periodic table?: Bottom lefthand corner 22. Nucleophilic strength increase with increasing what?: atomic size 23. Which alkyl valid would you expect to undergo Sn1 hydrolysis most rapid- ly? I, Br,Cl, or F?: I 24.In which reaction is a racemic mixture obtained? In which reaction is an inversion of chirality obtained?: inversion: Sn2 racemic mix: Sn1 25. Cleavage of an ether usually requires a strong acid that has a conjugate base which is a strong nucleophile,such as...? Depending on the type of alkyl group, the acid reaction with the halide ion produces what?: HBr HI alkyl halide and an alcohol 26. When chirality rotates clockwise the chirality is...: R 27. When chirality rotates counterclockwise the chirality is...: S 28. A solution containing equal amounts of both enantiomers is called a..?: - racemic mixture 29. A meso compound contains multiple centers but is neverthe- less because it possesses reflection symmetry: chirality achiral 30. For each chirality center Fischer projection - the horizontal lines are con- sidered to be coming of the page and the vertical lines are considered to be going the page _: horizontal - coming out of the page (towards you) vertical - going out of the page (away from you) 31. A racemic mixture of enantiomers is optically .: inactive 32. Based off chirality, how can you tell if two molecules are enantiomers?: If they contain the same molecules but one is S and the other is R 33. How do you convert a fischer projection to a wedge and dash diagram?: 1. place lowest priority on dash 2. place highest priority up 34. The a molecule is, the better/stronger nucleophile it is: - larger