(b) Provide the reagents required and the intermediate products involved in the following multi-step syntheses. Br LL F 3 steps HO3S. Br SPh 3 steps Br NO2

Br Brz CH3 CH3 H3C CH2CI2 H3C Br Electrophilic addition of bromine, Br2; to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl). In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br: :Br: .CH3 H3C H3C CH3 Br:

Provide the mechanism for the following reaction (1) PhMgBr (2 equiv) (2) H3O+ workup OH

What starting materials are needed to synthesize each azo compounds O2N H2N- -N=N- CI но -N=N- -CH3 I0 Fill in the reagent or starting material needed or product in each reaction a) CgH;CH;CH;CH2Br CGH;CH;CH;CH¿NH2 b) C,H;CH;CH;CH2CONH, CH,CH;CH;CH;NH2 HCI P-CH;C,H4NH2 NANO2 P-CH;C,H&NH2 HCI/H;0 P-CH3C,H4NH2 CH;COCI

What reagents are needed to synthesize the following bromides? Br Br Provide the major organic products obtained from the following reactions. a) SN1 CH;OH methanol b) DMF TsO Et CH;COONA SN2 Br, light

Provide the structure(s) of the expected major organic product of the reaction shown. 1) Disiamylborane 2) H₂O₂, NaOH OI O II ||| O IV OV CH3CH₂C(CH3)2C=CH OH OH xx xo IV

Give the major product of the reaction shown below. ? Cl₂ H₂O I CI IV Compound I O Compound IV Compound II Compound V Compound III OH LOH do you g V OH LOH

owing reactions proceeds via an SN1 or SN2 of the reaction: (b) S2 pro85 39 Br tort atubong auonsV HMPAnoitutitadua

122. For the following three step conversion of A to B, the appropriate sequence of reactions is A OH CAREER ENDEAVOUR B CHO (a) MnO₂; (CH₂OH),/p-TSA; PCC (b) PCC; MnO₂; (CH₂OH)₂/p-TSA; (c) PCC; (CH₂OH)₂/p-TSA; Jones' reagent (d) Jones' reagent; (CH₂OH)₂/p-TSA; MnO₂.

Write the mechanism, as well as the structure of intermediate A and product B, for the following reaction. -CO₂Me A OOH B