Lab Report: Reactivity of Organic Halides in Nucleophilic Substitution (Exp. 9) 40 pts/max
NAME: Shawn Vuong
SECTION: 145
1. Build the row of reactivity of halides toward sodium iodide in acetone? Explain the observed
order. (5 pts)
The order of reactivity is 1-brombutane, 1-bromo-3-methylbutane, 1-chlorobutane, 2chlorobutane. This is the order because Bromine is a better leaving group than chlorine and in Sn2
reactions primary halides react better than secondary halides.
2. Build the row of reactivity of halides toward silver nitrate in ethanol? Explain the observed order.
(5 pts)
The order of reactivity is 1-chloroadamantane, 2-chloro-2-methylbutane, bromobezene.
Because the first one has no steric hindrance and is simple tertiary, the next one is a cage-like tertiary
halide, and the last will form a secondary carbocation which reacts the slower than tertiary in Sn1.
3. Build the row of reactivity of halides toward silver nitrate in a 50% aqueous solution of ethanol?
Explain the observed order. (5 pts)
Order will be the same except reactions will go faster in the 50% aqueous solution of siliver
nitrate and ethanol because water is more polar so the carbocations will be more stabilized and thus
form faster
4. Open the UCAN program. Which bond breaks on the first step of the SN1 reaction? (3 pts).
The Carbon-Bromine bond was broken in the first step of the reaction.
Open the ORA program. Which of the three steps of the shown example is not a necessary part of the
SN1 reaction ? (2 pts).
The third step is the unnecessary step of the SN1 reaction in which the HOCH molecule
removes the extra hydrogen from the organic product.
5. What of the following statements is true for an SN2 reaction? (5 pts)
a. Inversion of configuration occurs at the step of an intermediate
b. Inversion of configuration occurs at the step of a transition state - True
6. What is the distance between hydrogens of the methyl group and the closest hydrogen in the axial
conformation of methylcyclohexane? (5 pts)
The closest hydrogen to the methyl group in the axial conformation of
methylcyclohexane is 2.52 Angstroms apart
7. What is the distance between hydrogens of the methyl group and the closest hydrogen in the equatorial
conformation of methylcyclohexane? (5 pts)
The closest hydrogen to the methyl group in the equatorial conformation of
methylcyclohexane is 3.16 Angstroms apart
8. What is the computed energy of the most stable conformation of butane? (5 pts)
The computed energy of the most stable conformation of butane is 1.12