Question

A student wants to synthesize the bromide of 3-methyl-2 pentano ve the IUPAC name of the main de product would you expect if you used the s Nabrand concentrated uric acid identify the mechanism (eg. SN, SN E1 E2) What is the best reagent you could use to obtain 2-bromo-3-methylbutane as the major product? 5. Explain why these reactions will the desired product. HINT: Identity the nucleophile and the leaving group in your answer a) ONE. OH олон 6. Identify the mechanism (Sx1 or S.2) for the substitution product of the following reactions Draw the substitution product. Br a) + MONO — MeoNa OH

Answer 1

4. CH₃ - CH - CH - CH₂ - CH₂ OH 1.H₂SO4 → 2. NaBr CH₂ - CH-CH CH₃ Mechanism: CH₃-CH - CH-CH₂ CH3 Ho-s-oh :OH CH₃ CH3 снен — сH - cң, сна H-OH2 -H₂o Br CH₃-CH - CH - CH₂ CH₃ си, This is a sN2 reaction. This is the not the best reagent as it can form stable carbocation. But if p-Toluene sulphonyl chloride reaction with alcohol than it is turned into a good leaving group for SN2 reaction only, O - CH₂-CH-CH-CH₂CH3 CI- CH3 CH₃ = vir T OH ! CH₃ - CH-CH-CH₂ CH3 CH3 NaBr py a Hel OTS CH₃-CH - CH-CH₂ CH3 CH3

O Na -OH tom Mechanismi ОН NG 011 nucleophile IO leaving NaI group s Na NOT FORMED Mechanism: se ona formed H₂O COH or reaction happened in polar solvent If acidified or not formed protic

+ Meo Na - Tymor o me Jura, CH3 Mechanism: Me uno Me " CH3 This is a SN2 reaction as Nao Me is good a nucleophile. Mechanism: се This is a sNI reaction.