Show Attempt History Current Attempt In Progress Tetrahydrofuran Thf Can Be Formed By Treating 1 4 Butanediol With Sul 1 (25.35 KiB) Viewed 15 times
Show Attempt History Current Attempt In Progress Tetrahydrofuran Thf Can Be Formed By Treating 1 4 Butanediol With Sul 2 (21.45 KiB) Viewed 15 times
Show Attempt History Current Attempt In Progress Tetrahydrofuran Thf Can Be Formed By Treating 1 4 Butanediol With Sul 3 (11.81 KiB) Viewed 15 times
Show Attempt History Current Attempt in Progress Tetrahydrofuran (THF) can be formed by treating 1,4-Butanediol with sulfuric acid. Propose a mechanism for this transformation OH M,SO HO 1,4-Butanediol Tetrahydrofuran (THF) 13.31 Your Answer Correct Answer Correct. The roup getting displaced is on a primary carbon, so an Sy2-type mechanism (backside attack) is favored and 5.1 is highly likely unstable primary carbocation. In order to make a good leaving group, one oxygen atom will be protonated by the strong acid before intramolecular nucleophilic attack by the other skygen atom. This forms aring and deprotonation of the Gonlum lon affords the final product This substitution reaction is expected to be similar to an 2 mechanism, involving back side attack
Correct. The group getting displaced is on a primary carbon so an S2-type mechanism (backside attack) is favored, and Sy is highly likely (unstable primary carbocation). In order to make a good leaving group, one oxygen atom will be protonated by the strong acid before intramolecular nucleophilic attack by the other oxygen atom. This forms aring. and deprotonation of the oxonium ion affords the final product, This substitution reaction is expected to be similar to an SN 2 because the leaving group is on a carbon that is protonation of the diol mechanism, involving back side attack primary The first step of the mechanismis water e Textbook and Media Hint
13.31a Add curved arrow(s) to draw step 1 of the mechanism. Modify the given drawing of the product as needed to show the Intermediate that is formed in this step. HO HO HO Edit Drawing
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