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 in the boxes below

Answer 1

A = i) Nanih ii) har E = i) Pol- Basocol H2 ii) NBSThy ivi) H, I Pd G= ï tBuok It Buch ii) Og! THE Zn-tho 910-912_3_910 - ū a H= Meona Imeon me me me-6-11-112 C1 C-CH₂ me me-cach-ch-CH-CH-me me me ome I

Answer Answers ECONO + >=(JH²+ Na NH TA = i) Nanila ii） \3 Ciotti & 3 } |. L /H 2. nicPI3A | lightly Trans-aikene ༡༽བ་ལས། སོག་མ།། ་ རྩམས། དང༌ ། དེ་ནས་དང་བསྟན་ c1 - L chc-Cly" O .amole ffc| y — clz C\ - =( – H 2. Imole HT mechanism cl v -c= —c=c- ft=c| ། more stable ༈ – 2-hyper conjugahve Structure 4 cl - : -:ཁc t,། བྱེ—ci, - རས་པདང་། – ར - ། te Dore stable

• tack * tcacy ped-Baso4s y H2 NBS lhv I allyllic Brominabion H2 me í me c-ch-CH2-CH-CH-CH3 kpd Сio Hot Br NMR-Signal Asigment ™F 3.91414) 3.969,"chan - 0.8(d, CH) CH3 i (13 ~ 0.8(d, 6H] 0.9(594) 4063 0.9 (s. 9H). /1154 Ch CH CH-CH-CHI 2.0( 18 ) 2 to 171924) (t, 24) me me Meco Na * 1. I me -CH=CH-me me me ме-с-си-си- me equipo me ron na parang -- Dec -CH-CH-CH-Chme meon me Ome G1H240 I NMR- Signal Asignment -I 3.419,141) a me l meg hold, 6H) Los me-c-ChCh CH-CH-met i me I ł ome I 0.965,9H) 3.0 (m, iH) 1-2t, 24) 1.419. 21)

me me me Budk me-¢-CH-CH-CH-CH-me me Brº ? Ei eliminaban tBuoH me ne--- bhc-me ? ? me F 11,2 ? shift Clot21 Br me - me me-e-CH2 C11 th cell me-c-12-114 117-C=CH₂ - me 121 poden com me=p-con-cn«n- & ous 12) Zn oroms me [G = ijt Buck me-¢-CH ₂ CH me tBuo Callie. I ü) OzITHF zn or DMS NAIR Signal Asignment-I 2.46+) me 0.4(s) / me-4-ch-Chy-Chec. s me Eriti 2.2(5) 1-3(+) 1.5(quintet)