Question

Mini-Spiderweb (16 pts, 2pts/box). Please complete the following reaction spiderweb with the appropriate starting materials, reagents or products. Pay attention to stereochemistry, and for product boxes – include only the major product(s), unless otherwise noted. E1 and Sn1 (5 pts). The following alkyl halide will undergo both E1 and Sn1 mechanisms to give a slew of products when exposed to water. Please draw them all in the box below. Remember to consider rearrangements and account for all stereoisomers formed.

Mini-Spiderweb (16 pts, 2pts/box). Please complete the following reaction spiderweb with the appropriate starting materials, reagents or products. Pay attention to stereochemistry, and for product boxes - include only the major product(s), unless otherwise noted. H2O H2SO4 H2009 LOCH OH TsCI pyridine SOCI NaOCH pyridine E1 and Sn1 (5 pts). The following alkyl halide will undergo both E1 and Snl mechanisms to give a slew of products when exposed to water. Please draw them all in the box below. Remember to consider rearrangements and account for all stereoisomers formed. H20

Answer 1

B-elimination Hydrohalogenation Naoet. OH 420 HBV H₂SO4 Hydration LocHz. CH3071. dehydration #2504/ hydro Hapo 4 -ots Tod Naoc ch. Pyridine socla Pyridine Dehydration CH₂oh E2 ③ SN² Naoctz

B-elimination Hydrohalogenation Naoet OH HBY LOCH₂ I CH₃OH Hydration dehydration (#2504/ Hapo4 -OTS Isch ott sock sel Naochz IV Pyridine E2 cha Pyridinel Dehydration SN² Naoct3 Ei + Bro SNA Der Hot Do I Reme