Chapter 7 Week 8

Chapter 7 Week 8 - Reduction using Metals(Na/Li in NH3...

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Unformatted text preview: Reduction using Metals: (Na/Li in NH3 + Alkyne) Mechanism: (9 G) 69 m ’NK . E‘— +uMa 4N2 In fin P3141 l1 N a +N 1 a; f, R -—3 a w; A M 4m? m3 M( k /*/W :1 l1 Steps (in words): Stereochemistly: @WIFNMw-‘mmd‘éuw ,1 ® warm ~ A Wm; Regmseewm W 04km @ W M; wn‘h M Other considerations: GD ”M 4‘ ““3 4% quad $on Example Problems: 0%“ .217 NH 3, Catalytic Reduction with Lindlar (HZ/Lindlar + Alkyne) Mechanism: AS: “a. “4ka ”'7 (\u (D H Steps (in words): Stereochemistry: ® LMMW is Snatch J” Regioselectivity: C15 quay»? .9323 M Other considerations: Example Problems: H2. l 1 ——~ Le (MAN: Afio L‘mllu- Ag \Fk Hydroboratioanrotonolysis: (BH3/Acetic Acid + Alkyne) Mechanism: (D (3 .fi H943 )1 /\._ 4 ,___7 /\fi ‘ on "" /\f\ 2- Jim f1 8"" H H Steps (in words): . Stereochemistry: ‘ . n n M an e. (D («Mt-Lu A B 99*. C ) Regioselectivity: a3 aim @ A'Le’l'b" M”, Other considerations: debuts Q4 “1*“ Fri“ Example Problems: Vk / // L6H”) \ gm fl Q "*2”. a 9" 0" ' \ com sY i0“; Acid Catalyzed Hydration: Mechanism: 1" non‘ f"\ CD ® 9) “,5, 6’) Steps (in words): (D11 SM 4' H, La“ ‘0 fimmfih‘a) @MT ooh EKMQO‘MN 0, ww-Hc 6J9. Cab-M 63d: t-wm @mfimw 65 Add 94mg“ erMj (”Braillwi @ {Miowwfiziin ple Problems: 0/1“? ”3"” __;, mm Catalytic Reduction: Mechanism: /\ by 1'. (9 @ Steps (in words): _ 6) saw/~- 6» £4 018 m1fi-fih4fll @ M I‘M-H714 Example Problems: ax? 4“ “31M ——~7 (HZSO4 + Alkyne) Stereochemistry: R . 1 ti , WhoutmLof e lose ec v1 : g t” W w? {M not, Other considerations: CAM M W WE. W “3 5% 7 N (112 + Alkyne) Stereochemistry: Regioselectivity: QHCOVLQ, Other considerations: "FEW Hydroboration-Oxidafion: (BH3/HZOZ,Na0H + Alkyne) Mechanism: //\/ 16“ F] M 1112111159.} J\§\H 71W CD Steps (in words): Stereochemistry: (015 rF fill/(W (Dileffivobu‘d‘lv‘ (5“— 651.6) ow l Regioselectivity: CC two 3 (9 WRM J“ W Other considerations: AM i“ W L, lad-«W Example Pro lem (9 0/ b 1 a 11.011 jig/WV 1. 111mm» Hydroboration-Oxidation with hindered base: ((sia)ZBH/H202,NaOH + Alkyne) Mechanism. H (.9101); “Mfipfl’l H M + l- _ __ NWJ’H—fl ij; ““1 j /\,f<m :7 I1 0 (5 o 6) Steps (in words): . Stereochemistry: NA CD Hmamau rwl; awu wlh l “A AllugN- Regioselectivity: dmzlliwdv-Elza ...7 C_5 @ $91. an. 6 {u- WtMfi“ ‘F‘l'1 Other considerations: @ikfli-th‘iw ls dial/«0&9 Example Problems: \. . ' \* L8H (“A”) l . BHCSl‘n'll '1 W anuwz‘ [W 7 Mg 9,. Mimi); Addition of X2: (XZ + Alkyne) Mechanism: Sr mm “Eon +5n1-a._L/ .53 H 1‘ or gr (l) @ Steps (in words): Stereochemistry: a“, “M4“ (DWX 63,5 al {cull/*4 R' 1.. 2% t : 341. w ‘ (. (6W Wk) eglose ec 1v1ty (9 Mi 4 ‘orb 4” illfiw‘i Col“ g) Other CODSIdel'athIlSZ Example Problems: Bil ‘/// 39% 0* «a N —a Addition of HX: (HX + Alkyne) Mechanism: fl> r“ 99 I” 0 N /‘I a“: flea-:0! + ha .1 wcan-cm -=: --C_':—c\ L Me: A WQ'G-‘f a Y m I if \H 6 ,9 or 5r 3, a: CD © ‘9 e) @333 Sin {refit Saul ,, my! % C.C. StereOChemi-WYinlwva‘, £0 J, (“who“"ll‘w ) Regioselectivity: m . 6) k6 Mal-S Wt i‘ . C. W E?) Oar-A M A H NLrlleL (pk 6,) Other considerations: g RIO QMQ Wm.“— Example Problems: Week 7 — Chapter 7 Chem 30A - Alkynes (Base/Primary Halogen + Alkyne) COW” Alkylation of Acetylide: Mechanism: 0. /-\> mammal ———» Haze + N _,, Mesa—V :7 .M cam; 3n) 42mm s; Base) (9 ® L___i v MW Steps (in words): (D MSaSL DBMM'i” aikbhe 6.3 514.5% A3 mace {1; l’ Mid: Example Problems: Stereochemistry: NA Regioselectivity: |° {Link Other considerations: 6% +Lml~lk1 _.7 0V [maul-1 3.. me» Br 1. MM“, Synthesis of an Alkyne from Alkene: (X2,Strong Base + Alkyne) Mechanism: :\ + B’}. "—77 a + ’0‘th .—-'r N + N‘Nl‘z —" 71‘ z. N H h 3,. B’- CD ® (9 Steps (in words): Stereochemistry: 6) 5.22 0h. B Lam _ , , , Regioselectlwty: @Clmm-fik 4 MW 53 64mg 8‘48 ® M git/mink J; h! W 1', Mia ”(it)” Other considerations: M \‘(Sr Mus-l ‘oe Example Problems: NJ“ in end/l ow C] L572 / e 9.1}!st ' /, L W1 qwllle‘iq. ...
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