{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

PS_4_KEY - T03 lZeAa‘ Problem Set#4 Suggested Carey 7th...

Info iconThis preview shows pages 1–8. Sign up to view the full content.

View Full Document Right Arrow Icon
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Background image of page 2
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Background image of page 4
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Background image of page 6
Background image of page 7

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Background image of page 8
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: T03) lZeAa‘ Problem Set #4 Suggested, Carey 7th Edition questions: Chapter 15: l5.30; l5.39; l5,;544 Omit). its Ms 1:4; iamjlmm W33 Predict the product for the following transformations. When necessary please explicitly show the stereochemistry of the product. o | 0%0. 0 Me ,OH HOM DMSQ, EtsN CHZCIZ Me —7s-—.15°,c MW Wilt-Wm \ I / OH Me |}l Me . O. i ,, NaOC|,THF "Ph 0°C Tam?!) Otifiuk‘a w O I HQH Me 0H. Ph/R<Me . PhH, reflux Me (I) 0 9 N/ Cl~(l31r-O€' 13““ “+9 0 PB” (ii) PhMgBr, Et20 $0)qu (iii) H30+ (iv) Swern Oxidation (V) flMgBr ,Eth ' Cc“ ‘ £4 (Vl) H30+ , (l) 0 ngBr, Eth H . - (iv) A020, DMAP GH20l2 “1“ .A .AA (i) YMQBI- , $20 (ii) H3O+ (iii!) 0504, t-BuOOH .« w t—BuOH, NaOH ‘ ‘5’“ (iv) HIO4 an m h k‘ {NA 1: ”M (I) chI'QO-f. H2804 —-—————-> (ii) EtOH, PhH OH reflux (i) O . OH t-Bu/U\CI pyridine : 2 Me (m 03. me) ~73 AcOH i‘ 49 9 CI 0 H R1/N N’RZ 02, Fe H H20 HS 2 equiv _4 ‘4‘; “Trims Me»? (i) Brz, H20 ({ Me (ii) NaOH, H20 M) mi)“ :baM MM 6-1] Wu ) Mew/\O/W/Me 02, hV Me M (i) KH, 18-crown—6 HO ‘6 .PhABr THF ' E (ii) Br2, H20 A gm) NaOH, H20 wM$¢b¢W 0k?“ 2%: WWI. mud/3w: BM SEC; mam finwka ‘0” NaOH, H20 t—Bu Br ‘3"?! \ H Eur h k 3. Rmvide the reagents to accomplish the fioliowing q‘ansformatiens. More than one step might be required. fer each transformatIon (£3 szM‘A .. In; 4. Provide a reasonable mechanism to account for the following transformations: o 5'“ -- M“ u 7 ”OH O h 0 ’0?ng HQCTO4 0 /3,—\1 H2804, H20 _ \\ h 0 /’Cf‘\ 5;“ [Z @ t BU % tBU @D GD 0“ lg‘fl’b I t] H6 a? \6 W9" $3” \83 , a) ‘5 (MA ‘ a “a ' " 1:3“ l K) “le L( ”*3 H 0 \ , a a o ’ W tau "‘ arm) H2304, H20 H H Me o Is / Wu. ‘39 Qt/jé‘v jés 90 0304 OH RBI ‘3 t-BuO H, t—BuOH (:E / OH O” i?" thO‘Oa is this molecule chiral? \o 99 o I? 5 ‘ 0/ $51 _____9 (7305/0 0N3; b ‘23}; manofia {0de “Qm'g “—9 awofiufi Ct 0‘045» 4, '0». “600% 99 hvoooaq v‘ \l/ or Al, DE? 130%: :9? be \X q :5 “name (I (9.... Q“ ‘3 on ” “x \ ° '1 on ‘1 ;- ‘35?" 4—... WM ‘ o, flo/J F’\> a CH O In your mechanism, please clearly draw the reactive ehgig cpnfotmer that leadsfio the epoxide m-CPBA, CHQCIQ ——————» o<> 5:?! Ar 12-] K \ Off a H ‘xuthfio - 5. Perform a retrosynthetic analysis on the following molecules (work backwards) from the given commercially available starting materials. OHC.,.,O,...CHO :> :> + ”002m I;\ a, ( 05001 5W0“! COQMG Q} m,” l Home“ ”$0“ “a“ 1le RUM ‘ / I: SEE; fly ~> 1” AWN, ...
View Full Document

{[ snackBarMessage ]}