Question

Arrange the following in increasing order of their boiling points : 1-chloropropane, 2-chloropropane, 1-chlorobutane

What is an ambident nucleophile ? Give one example.

Why do tertiary alkyl halides undergo SN1 reaction at a faster rate ?

Define Enantiomers.

Nucleophilic Substitution. Nucleophilic Substitution reaction of haloalkane can be conducted according to both SN1 and SN2 mechanisms. SN1 is a two step reaction while SN2 is a single step reaction. For any haloalkane which mechanism is followed depends on factors such as structure of haloalkane, properties of leaving group, nucleophilic reagent and solvent. Influences of solvent polarity : In SN1 reaction, the polarity of the system increases from the reactant to the transition state, because a polar solvent has a greater effect on the transition state than the reactant, thereby reducing activation energy and accelerating the reaction. In SN2 reaction, the polarity of the system generally does not change from the reactant to the transition state and only charge dispersion occurs. At this time, polar solvent has a great stabilizing effect on Nu than the transition state, thereby increasing activation energy and slow down the reaction rate. For example, the decomposition rate (SN1) of tertiary chlorobutane at 25 °C in water (dielectric constant 79) is 300000 times faster than in ethanol (dielectric constant 24). The reaction rate (SN2) of 2-Bromopropane and NaOH in ethanol containing 40% water is twice slower than in absolute ethanol. Hence the level of solvent polarity has influence on both SN1 and SN2 reaction, but with different results. Generally speaking weak polar solvent is favourable for SN2 reaction, while strong polar solvent is favourable for SN1. Generally speaking the substitution reaction of tertiary haloalkane is based on SN1 mechanism in solvents with a strong polarity (for example ethanol containing water).