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CHEM 231 Fall 2016 Problem Set 9 Nucleophilic Substitution Draw a structural formula for the most stable carbocation of each molecular formula. 4H9 c) C8H15 (d) C H O From each pair, select the stronger nucleophile. (b) CH3 CO0 or OH (a) H2 O or OH (c) CH3 SHor CH3 S (e) Cl or in methanol (f CH3 OCH3 or CH3 SCH3 (d) Cl or in DMSO Account for the fact that the rate of this reaction is 1000 times faster in DMSO than it is in ethanol. 1,3-Dichloropropane Propanedinitrile Draw a structural formula for the product of each S, 2 reaction. (a) CH3 CH2 CH2CI CH3 CH2 ONa ethano (b) (CH3)3NCHacetone CH2Br NaNacetone (d) H3人ã¬ã¼ ãã¼-cl + CH3SNa -ethanol. (e) CH3 CH2 CH2CI CH3CiC Lidietb ether CH2CI +NH3 ethanol NH+ CH3(CH2)6CH2Cl ethanol th) CH3CH2 CH2Br NaCN acetone Which member of each pair shows the greater rate of S 2 reaction with Ki in acetone? CI Br Br Page 2 of 5 Show transcribed image text
CHEM 231 Fall 2016 Problem Set 9 Nucleophilic Substitution Draw a structural formula for the most stable carbocation of each molecular formula. 4H9 c) C8H15 (d) C H O From each pair, select the stronger nucleophile. (b) CH3 CO0 or OH (a) H2 O or OH (c) CH3 SHor CH3 S (e) Cl or in methanol (f CH3 OCH3 or CH3 SCH3 (d) Cl or in DMSO Account for the fact that the rate of this reaction is 1000 times faster in DMSO than it is in ethanol. 1,3-Dichloropropane Propanedinitrile
Draw a structural formula for the product of each S, 2 reaction. (a) CH3 CH2 CH2CI CH3 CH2 ONa ethano (b) (CH3)3NCHacetone CH2Br NaNacetone (d) H3人ã¬ã¼ ãã¼-cl + CH3SNa -ethanol. (e) CH3 CH2 CH2CI CH3CiC Lidietb ether CH2CI +NH3 ethanol NH+ CH3(CH2)6CH2Cl ethanol th) CH3CH2 CH2Br NaCN acetone Which member of each pair shows the greater rate of S 2 reaction with Ki in acetone? CI Br Br Page 2 of 5
Show transcribed image text Collen VonLv2
24 Mar 2019