Week 4 Worksheet - Organic Chemistry II Week 4 worksheet Not for credit IR‘F‘ I'd-fie Apia/mid a Draw the mechanism of intramolecular aldo

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Unformatted text preview: Organic Chemistry II Week 4 worksheet Not for credit IR‘F‘ ' I'd-fie Apia/mid? a Draw the mechanism of intramolecular aldo! condensation of 4—methylheptane-2,6-dione to form 3,5-dimethylcyclohex- 2-en-1—one. You will need to perform the aldol condensation, foilowed by dehydration/eiimination of water. 0 O O 1) NaOH, H20 2) warm 0 x. 5“ 2‘: /‘L/l\i5 9’ [5:4 @ AL H K2955 H U / \ O 405 O 1)NOEt/EtOH ([9 H a / 6 bag [:5 7%». km”? fl PM 0 Product from reaction 1) NaOH, H20 ll immediately above 2) H20, H01 W 3) heat I) gami’ififxaliby‘ j ... \ 5 (.D N" <3 1) HUI/H20 ll Bf HCI/HZO O W —~—~ I 2) We / 2) 3) NaOH, H2O an. 4) HCI, H20 5“? 5) heat 6‘me 1) 1 eq. NaOEt, EtOH 3) 1 eq. NaOEt, EtOH 4) NaOH, H20 5) HCI, H20 6) heat 1) 0.9 sq LDA 2) O o O4 “a H, Qh‘ac/W 3) H20 Devise a synthesis (show the necessary series of reactions) to prepare each product shown in the retrosynthesis shown below. Remember: There are retrosynthesis, the final product is shown here on the left! You may use additonal reagents that contain no more than 4 carbons, plus any other atoms. 00 OD %0:M0/\ Below, you will have performed a mthod similar to the first two steps in the synthesis of the antibiotic Cipro: O o o F F c: O O OH :> EtoMOEt Cl or Cl Cl In this synthesis, which starting material supplies the methyl group at the 4-position in 4—methylheptane—2,6vdione? o o O o o WZNK Mo“ 20f2 ghoMfld b?— ,/ MaoMe/Aaofl- O Q {AJOEt‘ o . /L\ U 1;? if L M Méégfi <1.“ 0 e- 9 a? In 8’ w._> O O O O Dfl/aD/‘f— O E) (H— 63 OMQ “€1- /H o a (I: )1 DHfi J I 4m L) /Tb’r‘ U? CD CD @625 _c/ #10) _,_/ 7Lfan565M7/IICAJK/‘9fl 7 O‘F f4+ramo{€c_q/4;r 0:4 ld/eflLj/ KW ...
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This note was uploaded on 01/22/2012 for the course CHEM II taught by Professor G during the Fall '11 term at University of California, Berkeley.

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Week 4 Worksheet - Organic Chemistry II Week 4 worksheet Not for credit IR‘F‘ I'd-fie Apia/mid a Draw the mechanism of intramolecular aldo

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