Question

Clotis 1. Imole Hel 1.Li/NH3 -78°c 2. Mc PBA 2. 1 mole HI Kamaryu H NMR/IR VE c) H₂O FNne) (NMR/IR lCq H180 co ter) C10Hz, Br

Use the spectra above to fill in the letter spaces in the guided synthesis.

Answer 1

Answes TECONA A iNaNi2 CioHI8 .Li 2-mcPBA liqNH Tians-aikene Cl CiH c 2. Inole T mechanism C C oce stable 2-typc2 conjugahve Steuctre slable

NBS Cl Br H2 Pdl Base4 -cC5-d1-ei e CHC - e crs-alkene Pacval ceclucloa) Co121 1B6 BPlBas04 E = NnIR- Signal asignient- E. 3.5() .2 () 0-2(d) mecCil C- G-g (s) -)e 2.0(m) me me me Meoe me--cC;-CH-ci-me 21 e -сh си— си 1 CH-me ect e Cme e Su bstitutioo keach (SN2 mecharaism) CuH240 Mecec NmR- signal asignment- T 3.4(1) me o(d) me CH CH e -Ct mec 0.g(s) omme > e 3.0(m) 1-2() 3.4(s)

me De CH, -CCH- 1-01e 0e-C-CCibC me E1 eliminahon e tBuoH l,2 2shit С1оЧ21 Вr СИз me e- me , с- сH;- с ,и me G=tBucK me- CH2CHCH tBuo me 03TF Zn or Dms Cgll80 NIR Signal Asignment-I me me- 0q (5) me 2 2 (s -3(t) -5(quintet)