Question 14 Predict the FINAL (?) product (or a mixture of products) for the following synthetic transformation: 1) NaNH2 (excess) 2) H₂O 1) n-BuLi 2) Br 1.6 ABCD 00 OD A 1) 9-BBN 2) H2O2, NaOH NaBH MeOH ? B с OH -OH OH Na, NH3 MCPBA two enantiomers D OH

Starting with benzene, what is a possible product of this series of reactions?: 1) HNO3 & H2SO4 2) Fe, HCl 3) (CH3)2CH-Br, FeBr3 4) NaNO2, HCl, 0-10 oC 5) HBF4     2-fluoro-3-isopropylaniline     m-fluoro-benzenesulfonic acid     o-fluoro-isopropylbenzene     2-amino-benzenesulfonic acid

o OH 3) Please draw the structures that correspond to omitted structure for each of the following synthetic sequences. HO Cro3 Cl (d) Cro3 (a) Product `OH Product OH H30 H30 HO PCC Cl PCC (b) Product (e) `OH Product "OH HO РСС NABH4 (f) Starting Material Product 'OH ELOH

Reagent 3 list; commas separate the choices benzylamine,cyclohexlbromide, cyclohexylamine NaBH3CN catalytic H+, h30, NaOH Reagent 4 list; CH3(Ch2)2MgBr, cyclohexylamine NaBH3CN catalytic H+, Na2 Cr2 O7 H2O H2SO4,cyclohexabromide reagent 5 list; cyclohexylamine NaBH3CN catalytic H+,CH3(Ch2)2MgBr, cyclohexabromide, benzylamine

The following series of reaction steps will yield 1) But-1-yne plus NaNH2; 2) the product of Step 1 plus Butanone; 3) followed by H30* O 3-methyl-hept-4-yne-3-ol formic acid, propanal and butan-2-ol an octane-based compound containing both a ketone and an alkyne O CO2, propanoic acid and buta-1,2-dione O 4-methyl-hept-4-yne-1-ol QUESTION 34 Which of the following will not oxidize propan-2-ol to propanone? O chromic acid reagent O KMNO4 О МСРВА O nitric acid

Which reagent/catalyst would be expected to bring about the following conversion? OH CH;CH2CH,CH CH;CH2CH,C-H ÓCH, Ag(NH3)2" / OH CH3OH / H3O* (1) NaBH4 (2) H30* O HNO3 / H2SO4 O K2Cr207/ H2SO4

What is the likley product of the reaction sequence shown? MgBr MgBr ОН РСС H2O K,Cr207/H2SO/H2O H,O CH2ČI2 ether ether ОН HO || II IV V O II O IV O v

|| wwwwww wwwwwwww Benzophenone dissolved in ethanol (EtOH) reacts with 2, 4-dinitrophenylhydrazine (2,4-DNP) at room temperature (RT): ob NH2 HN NO2 EtOH RT benzophenone & NO2 2,4-dinitro phenylhydrazine

3) Draw the structures of the major organic product(s) for the following reactions. HI in CH₂Cl₂ 3 excess Cl₂ in H₂O H₂SO4 in H₂O (Two products) Br-Cl in THF 1) BH3 2) alkaline H₂O₂ OSO4 + HOOH

5) Complete the following reactions a) cH3- CHz COOH + b) cH3 - CHz CooHt LioH - c) CH3 COOH + Hg CO3