CH3 CH3 MsCI OMs occurs. The resulting sulfonate esters are reactive in Syi and SN2 reactions since the sulfonate group is a very weak base and is therefore a good leaving group Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Alcohols react with sulfonyl chlorides to form sulfonate esters. Only the O-H bond of the alcohol is broken in the reaction, and so no inversion of configuration CH3 :0 0: CH3 :CI: CH3 он

Q4. Alkyl halides are good at doing substitution (SN2/SN1) and elimination (E1/E2) reactions because the halide (X-) is a good LG. Alcohols on the other hand are not suitable for these reactions since hydroxide (¯OH) is a poor LG. However, an OH can be converted into a OTs (tosyl group) by reacting an alcohol with TsCl in presence of a base. An OTs is a good LG, and this allows us to indirectly (via OTs) use alcohols in substitution (SN2/SN1) and elimination (E1/E2) reactions. (4) OH TsCl NEt3 OTS Tosyl ester NaCN DMSO + HNEt3 Determine the major/minor products CH3OH heat OTS Tosyl ester TsCl = NaOCH3 CH3OH DBU Ś=0 CI

Complete the following nucleophilic substitution reactions. In each reaction, show all electron pairs on both the nucleophile and the leaving group.

When ethoxybenzene is treated with a mixture of nitric acid and sulfuric acid, two products are obtained, each of which has the molecular formula C8H9NO3. For the mechanism, draw the curved arrows as needed. Include lone pairs and charges in your answer.  Do not draw out any hydrogen explicitly in your products. Do not use abbreviations such as Me or Ph.