School of Physical & Mathematical Sciences e NANYANG Division of Chemistry & Biological Chemistry UNIVERSITY H3 Organic Synthesis and Mechanism - Tutorial 4 Alkenes and Alkynes 1) Determine the degree of unsaturation for the following molecular formulae: (a) CrHio (b) CeHi00 (c) CsHsBrCl (d) CcHeNO J Wey pr Woy et 2) Draw the products for the following reaction. The carbon backbone of open chain compounds should be drawn in their "zig-zag" conformation. Indicate the stereochemistry of the products clearly ae) 4, 004 & -_BNAHSOs HO A A AN t Cui or 1.0804 v 2. NaHSOs, HO Bro ” a —— — a wr ened ines 1. Hg(OAc)2, HzO 1. BHg, THF ©) - eee 2. He, NEOH ys 7 ——— —— oH MeQ et m% = Hp, Lindlar's catalyst V4 OH OO ° a 3) Suggest a synthetic route to the following compounds, The main carbon skeleton should be derived from the starting materials given. You may use any reagents for your synthetic route. Br cl =O cy ot, aa) oh, OL. ov (b) X from Ave } DRE era ve wey ke,Motes : © ood ty bose te fefatie pee tohee hein oF yuu Piducte - on OW ~ Pe BS FL eA t 2. Hohe, 4 MW The Oy coold ad) fe 2 OW is 1 Sym tenes ot — Mathes SYS bey te encotony I t on oo Obvione fame hy St Lt it oe remy compo) lene ap or gel, KA Pe atees Sysoely urSchool of Physical & Mathematical Sciences kgm TecNotocicaL Division of Chemistry & Biological Chemistry yay UNIVERSITY () AnRK from A aw 7 Br + enantiomer XW 9 Ml ae A Sor wat Seo “ “Lo AsL able, jak Bel x H (d) AAK from AQ nee OH + enantiomer 1119, Toltle) tps sere of ale » rh 1. Od, , of f Ask wb) SS~ re LAS on 4) With the use of curved arrows, show the complete stepwise mechanisms for the following reactions (more than one step may be necessary): @) on 804 or fa eho ey ote Hd 7 “yo Zs oR t wf ’ Ky 4 as" — nw a xX: any anion OM AA Jo Se Oe9 baw « _ Seg ~ Celmtoet, ) ot € » Ke iB ID rN? ay 5 le w&) Mita ser tote stncly, ho nine fle rechenm ey + + BA Ke, iO 1 4G Mae fle Bro tr 6 cerh boo and IF ir ag i to dépatenste -0-" signi bles ofl, Dont Eager your pha f hewn chevy = in deaf ts ay © meckentym, ty te eh vse Of tle lesyot vied. Avail gerwetty specter et “Mook weed, ep ate de ly cide, ce