Homework - Chapter 12 Chem 2320 I. Addition reactions of alkenes

Homework - Chapter 12Chem 2320I. Addition reactions of alkenesName ____________________________________1. Label the following reactions as a substitution, addition, or elimination.a)Cl(CH 3 ) 3 COKb)HClClc)ClNaOHOH2. What reagents would give the following products?a)OHb)Brc)OHd)Bre)OH(different from c)

HW Ch 12 p 22. Give the products of the following reactions.a) H 2 , Pd/Cb)H 2 , Pd/Cc)H 2 , Pd/Cd)H 2 , Pd/Ce)H 2 , Pd/Cf)H 2 , Pd/C3. Give five isomers with the molecular formula C 6 H 12 that will react with H 2 and Pd/C to give hexane.4. Give the product of each of the following reactions.a)KMnO 4H 2 O, KOHb)OsO 4 , H 2 O 2

HW Ch 12 p 3c)KMnO 4H 2 O, KOHd)OsO 42 eq H 2 O 2e)KMnO 4H 2 O, NaOHf)OsO 4 , H 2 O 26. Give the products of the following reactions.a)PhCO 3 HOb)PhOOHc)PhCO 3 Hd)PhCO 3 HOe)PhOOH

HW Ch 12 p 47. What alkene could be reacted with peroxybenzoic acid to give the following epoxides?a)d)OOb)Oe)OOOc)f)8. Give the products of the following reactions.a)CHBr 3(CH 3 ) 3 COKb)CH 2 I 2Cu-Znc)CHCl 3(CH 3 ) 3 COKd)CH 2 N 2h!e)CH 2 I 2Cu-Zn

9. Give the product for each of the following reactions.HW Ch 12 p 5a)Cl 2b)Br 2 , H 2 Oc)Br 2CH 2 Cl 2d)Cl 2 , H 2 Oe)I 2 , H 2 Of)Br 2CH 2 Cl 2g)2 eq Cl 2 , H 2 O10. What starting material and reagents could be used to prepare each of the following products?a) b)IBrBrc)OHd)ClBrBrOHBrBr

HW Ch 12 p 611. Show the polymer that would be formed in the following reactions.a)H 2 SO 4b)ClCH 3 OOCH 3heat or lightc)OH 2 SO 4d)CH 3 OOCH 3heat or light12. Show the mechanism by which polybutylene could be made using a carbocation mechanism. Builda polymer three units long, showing all steps. (Note that this reaction will require heat, since thecarbocation is secondary.)H 2 SO 4heat13. What alkene could be used to synthesize each of the following polymers?a) polyacrylonitrile(used in making carpet)N N N

HW Ch 12 p 7b) teflonF FF FF FF F F F F F(used in making non-stick pans)c) polyethylene(used in making plastic bags)d) polyvinyl acetate(used in makingsafety glass)O O OO O O14. Write out the reaction which will occur when 1-ethyl-1-cyclopentene is treated with each of thefollowing.a) osmium tetroxide and hydrogen peroxideb) diiodomethane and copper-zinc couplec) mercuric acetate and water, followed by sodium borohydrided) peroxybenzoic acide) hydrogen gas and palladium on carbon

HW Ch 12 p 8f) borane-THF followed by hydrogen peroxide and hydroxideg) chlorine gash) hydrochloric acidi) potassium permanganate, water, and sodium hydroxidej) chloroform and potassium tert-butoxidek) hydrobromic acid with a trace of organic peroxidel) diazomethane and heatm) phosphoric acid and watern) iodine and water

II. Stereochemistry of alkene addition reactionsHW Ch 12 p 915. Give all stereoisomers that would result from the following reactions.a)CH 2 N 2heat or lightb)H 2 Pt/Cc)Cl 2d)PhCO 3 He)I 2H 2 Of)HClg)OsO 4H 2 O 2h)H 2 SO 4H 2 Oi)1. BH 3 -THF2. H 2 O 2 , NaOH

HW Ch 12 p 10IV. Oxidative cleavage of alkenes16. Give the product of each of the following reactions.a)1. O 32. (CH 3 ) 2 Sb)1. O 32. (CH 3 ) 2 Sc)1. O 32. (CH 3 ) 2 S1. O 3d)2. (CH 3 ) 2 Se)1. O 32. (CH 3 ) 2 Sf)1. O 32. (CH 3 ) 2 S17. Which of the previous reactions above would give a different product if reacted with ozone followedby hydrogen peroxide? For those that will, draw the new products.a)d)b)e)c)f)

HW Ch 12 p 1118. What alkene would give the following products after ozonolysis?a)HOOc) andOOb)OHOd) andH OHOOHV. Synthesis using alkene reactions19. Fill in the starting material and reagent to form each of the following products.a)OHb)BrBrc)BrOHd)OH

HW Ch 12 p 12OHe)Clf)OHg)HOOBrBrOh)i)OOj)+OH

HW Ch 12 p 1320. Three different types of peroxide are used in alkene reactions. Explain what each is useful for.Oa)O O Hb)H O O Hc)H 3 C O O CH 321. Explain where each of the atoms that is added to the C=C comes from in the following reagents.a)1. Hg(OAc) 2 , H 2 O2. NaBH 4OHHb)CHCl 3KOC(CH 3 ) 3ClClc)PhCO 3 HOd)1. BH 3 -THF2. H 2 O 2 , NaOHOHHe)H 2 SO 4