Question

(1) What mechanism do you believe will be favored with Nal in acetone? What order of reactivity do you predict will be observed when each of the alkyl halides in Figure 1 is reacted with Nal in acetone? Complete the below table; list the relative ranking of the reactivity of the alkyl halides and your reason for placing that alkyl halide at that ranking. Write your prediction of the mechanism and the order of reactivity with Nal in acetone as a hypothesis. Justify your hypothesis. Relative ranking (#1 - #7) Reason for ranking 1-chlorobutane 1-chloro-2-butene 2-chlorobutane 1-bromobutane 2-chloro-2-methylpropane bromobenzene benzyl chloride

Answer 1

(0) - Restone is a bolor mon-botieboluruk HAR protie solvents tend to favour 5m2 alaction Thus, the alkye halides shall tend to t 5.2 bathway. Now, we must look at the nature of alkyl halides to determark rank them in reactivity 01 can be ud at first granu Haut bromsbe ad E m ot Yurt out all as it is on omatit ? and thus would never undergo reaction, trans focussing on alkye halides, the primary halides shall be more reactive than secondary halides. How Furthermore, the SN2 bathway is favoured by large Teaving groups. As Bromine is a better leaving group than chlorine, chlorets - bromobutane & hall be more reactive than -chlorobutane. Ab 2-chloro 2 metus propane is a 2-hallide, it shall be very less reactive. Although 2-chlorobutane is a zo halide it shall be more reactive than the formers Now; benzyl chloride Phraa is a very reactive alkyl halide due to the al effect of bengene ring , facilitating SN2. This makes it most reactive also contains a double As 1-chloro -2-mthay butene come , it shall at no 2 as bond far as reactivity is rank them as : Hence, we can concerned. benzyć chloride ? 1. chloro-2-butene) I- bromobutane) butene 1 bes bromo ben gene 5 2-chlorobutaney 2-chloro-2-methyl } T-chloro butane is : she reaction mechanism SN 2. autone Rx & 1