Q19 Br OH Br A) NBS P) NaBH4, CH3CH2OH B) Br2, CCI4 Q) CH3CH2ONa, CH3CH2OH AD) C

Question

Q19

Br OH Br A) NBS P) NaBH4, CH3CH2OH B) Br2, CCI4 Q) CH3CH2ONa, CH3CH2OH AD) C) Cl2, CC R) 3)3 3)3 A AE) S) NaNH 2, NH3 D) HBr Na, NH E) HBr, ROOR AF) U) H2 F) H2O V) O3 G) Hg(OAc) 2, NaOH, H2O O O W) Zn, CH3COOH H) Hgso 4, H 20, H2SO AG) X) CrO3, H2SO4, H2O Hao (workup) Y) CH3CH2Br J Dicyclohexyborane CH3CH2CH2Br K) BH3 AA) CH3CH2Li L) H2O2, NaOH, H2O AB) CH3CH2CH2Li AH) M) Pd Al) N) Lindlar's Catalyst AC) o) 1% Pd (OAc) 2, R3P Look at the given synthesis and the provided reagents. Fill in the blanks with the single letter code of the appropriate reagent, or the appropriate descriptive vocabulary word/phrase to complete the description. Remember the computer is very literal so check your spelling carefully.

Explanation / Answer

First we add B reagent followed by 2 equivalents of reagent S followed by I workup to give the functional group alkyne. Then we add reagent S followed by AH and F workup to give the (functional group) alkene with E stereoselectivity. Lastly reagent T will give the final product with E stereoselectivity.

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