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 TSCI NEt3 OTS Tosyl ester NaCN DMSO + HNEt3 CH3OH heat СР Determine the major/minor products OTS Tosyl ester TsCl = NaOCH3 CH3OH DBU --0

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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
Transcribed Image Text: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
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