Question

1. Compare the reactivity of primary alkyl halides in part 1 (SN2) of this experiment to the reactivity of primary alkyl halides today. What conclusions, if any, can you make about the reactivity of these molecules under these different conditions? Use specific data to make your point.

2. Compare the reactivity of secondary alkyl halides in part 1 (SN2) of this experiment to the reactivity of secondary alkyl halides today. What conclusions, if any, can you make about the reactivity of these molecules under these different conditions? Use specific data to make your point.

alkyl halides used in experiment:

1-Chlorobutane

1-Bromobutane

2-Chlorobutane

2-bromobutane

2-chloro-2methylpropane

SN2 reaction times(in minutes) in 18% NaI in Acetone:

1-Chlorobutane - 23

1-Bromobutane - 2

2-Chlorobutane - 21

2-bromobutane - 18

2-chloro-2methylpropane - 9

SN1 Reaction times(in minutes) in 1% AgNO3 in Ethanol:

1-Chlorobutane - 9

1-Bromobutane - 9

2-Chlorobutane - 9

2-bromobutane - 5

2-chloro-2methylpropane - 2

Answer 1

18 Na I Acetone 1-Chlonobutane SN2 18 NaI Bm Acetone 1-bromobutane SN2 187. NaI Acetone 2-chlonobutane SN2 187. NaI Acetone Br I 2-bromobutane SN2 18-7. NaI A-eetone SN2 2-chlono-2-methyl popane

Ih SN2 neaction, the nucleophile attacks from the back side of leaving aroup SN2 neaction in a'single step.

The onder of neactivity of aly balides towards a nucleophile in a SN2 neac tion is- -alkylhalide 73-allylhalide 1- alkyl halide stenic hindnence anound Beeause the leaving group incneases fnomprimany ( alky halide to tertiany (3) alkylhalide Thus the neactivity of a nucleophile increases foom 3 alkyl halide to 1 alkyl halide

Hense meaction time of SN2 neaction of alkyl halide has the follouing 2allyl halidealyl halide 3-alkylhalide ondem Hene, 1-chlono butane and 1- bnomobutane ame prmimany alkylhalide 2-chlonobuane aud 2- bnomobutane secondany alkylhalide 2-chlono-2-methypmopane is terhan ame alkay halide SN2 eaction also depends on the leaving noup. leaving pmoperty of a gnoup othe SN2 meaatin nereases. then the nate ineneases Hene, leaving propermty of B is qreatem than e

Thene-fome e aet the follouing neaction time fon SN2 neaction 1-cblonobutane 23 (A bnomobutane 2- B 21 2-chluno butane 2-cblono-2-metpropone-q 18 2-bnomo butane-

17. Ag NO3 Ethano el 10-cambocation Bn 6thano) 1-Cambocation SN1 2°-eambocation ST 22 Cambocatio Br

2-cambocatim foomatim SN PRDtiom involves OP cambocation intemmidiate . With the stability of cambocation the nate ot SNi neaction incneases, imcneasing

The onder of cambo catim stability is 3° 20 SN NDCtmate also depends on the leavinganoup. TP the leaving phopem o a gnoup increases then the neactiom mate also incneases. 2-chlono-2-methylpropane frmm s 3 cambocatiom. So SNi neactim time of this compound very lou (2 mins Betweon 2-bwomobutan.e adchlomobutaue 2-bnomo butane has SN Reactim time Lowere than that of the 2-chlonobutane as leaving propery of bnamo is neaters than chlomo . ahoro butane aud 1-bmomobutane cam fonm 9-cambocatim eactionand 1 cambo eafiom has Jow stability. Thus neactim time of these duning SNd

alkyl halide will beaneaten than that of the othem 2 aund 3 alkyl halides. Hense we found the SN Meactin times in 1. ANO3 in Ethamol t-ahlono butane q bnomobutane-9 Chlonobutame9 2 2-bromobutane5 2-Chlono-2-methylpropane>2 L