Question

Relative ranking (#1 - #7) Reason for ranking 1-chlorobutane 1-chloro-2-butene 2-chlorobutane 1-bromobutane 2-chloro-2-methylpropane bromobenzene benzyl chloride (2) What mechanism do you believe will be favored with AgNO3 in ethanol? What order of reactivity do you predict will be observed when each of the alkyl halides in Figure 1is reacted with AgNOs in ethanol? Complete a similar table as in question #1 for these reaction conditions. Write your prediction of the mechanism and the order of reactivity with AGNO3 in ethanol as a hypothesis. Justify your hypothesis.

Answer 1

In presence of polar protic solvent like C H50 H (ethande) AgNO₃ Can be readily ionized to form Agt' and nog ions. R-% + Ag" no3 R + Agxd + 1103 (More stable carbocation) Ease of reactivity 2 with AgNO₃] } a & Stability of Cambocation rate = k [R-x]' - Oxdev = 1) b) Relative Ranking: . (Allyl carbocation) trom I-chloro-2-Butane (Benzyl Cation) 30 Carbocation (2-methyl propylian) ( 1 - Carbocation) a from (2-Corbo cation) from 2-Bromo bulane (2-Carbocation from 2-chloro butane 1- chloro butane (phenyl Carbo cation) from Bromo benzene c) Reason for Ranking: Order of stability of Carbo cation decides the reactivity because after removal of x'atom the resulted Carbo- Cation must be more stabilized. The order of stability of Carbo cations is 3 - Carbocation > Benzyl > Allyl > 2 (Bromo) (Chloro) 2 l cation > Bromo Benzene d) In presence of caH5OH AgNO₃ is completely ionized- Hence Rate of reaction depends on the concentration of Alkye halice (Rx) only. Hence the order = 1