Nucleophilic Substitution Lab Report Hong Chang 12/01/11 Dr.

Campbell

Nucleophilic Substitution Abstract: This report presents nucleophilic substitution experiment to understand Sn2 and Sn1 reactions. Five different alkyl halides (1-chlorobutane, 2-chlorobutane, 2-chloro-2methylpropane, 1-bromobutane, and 2-bromobutane) were used and mixed with 18% NaI for Sn2 reaction and 1T ethanolic AgNO3 for Sn1 reaction. Mixtures were observed, and the time it took to form precipitation was recorded.

Introduction: Nucleophilic substitution is the reaction of an electron pair donor(nucleophile) with an electron pair acceptor(electrophile). An sp3-hybridized electrophile must have a leaving group in order for the reaction to take place. The term Sn2 means that two molecules are involved in actual transition state. Nucleophile takes over the place of the group as soon as they leave. Unlike Sn2 reaction, however, in reaction s1, a planar carbenium ion is formed first, and then reacts with nucleophile. Therefore, rate of reaction can be determined depends on how easy the group leave. Good leaving group, such as halides, will have faster rate of reaction than those with bad leaving group. In this lab Five different alkyl halides (1chlorobutane, 2-chlorobutane, 2-chloro-2-methylpropane, 1-bromobutane, and 2-

bromobutane) were used and mixed with 18% NaI for Sn2 reaction and 1T ethanolic AgNO3 for Sn1 reaction. The purpose of this lab is to make an precise observation how five alkyl

hides reacts in different condition and be able to explain why that happens.

Procedure: Two sets of 5 test tubes were prepared with 5 drops of each alkyl hides(1chlorobutane, 2-chlorobutane, 2-chloro-2-methylpropane, 1-bromobutane, and 2-

bromobutane). Then each set was divided into two different groups, Sn2 and Sn1. For group Sn2, all five test tubes were added by 20 drops of 18% NaI. Test tubes were observed to see if precipitation forms. Those test tubes that did not form precipitation within 5 minutes were put into 50C water bath for another 5 minutes. The time was recorded as soon as they formed a precipitation. For group Sn1, the test tubes were added by 20 drops of 1% ethanolic AgNO3 and mixed well. The time were recorded, however, the reaction was marked no reaction if no precipitations were formed in 5 minutes.

Data

SN2 1-chlorobutane 2-chlorobutane 2-chloro-2-methylpropane 1-bromobutane

SN1

1min 30sec NR

1min 30sec NR

2min 30sec 10sec

10sec

5sec

2-bromobutane

1min

5sec

Conclusion: 1-bromobutane in condition Sn2 was only akyl halide that reacted immediately with 18% NaI. Rest of akyl halide formed precipitation within 5min in 50C water bath. In condition Sn1, 1chlorobutane and 2-chlorobutane had no reaction, because Sn1 does not react with primaries. And because Sn1 works best with tertiary, 1-bromobutane had the fastest reaction time. And because Br has longer chain than Cl, Br-C bonds were easier to break.