1. To produce tert-butyl chloride from tert-butyl alcohol
2. To understand the SN1 and SN2 mechanism involved in the reaction
3. To determine the yield of percentage of t-butyl chloride
Tert-butyl chloride, also known as halo alkane or halogen alkane is a hydrocarbon group which contain at least 1 halide atom attached to its molecule. tert-Butyl chloride is a colourless, liquid organic compound at room temperature and it is highly flammable and volatile.
Tertiary alcohols can be converted to their corresponding alkyl chlorides by the addition of concentrated hydrochloric acid to the alcohol. In this experiment, concentrated HCl is added to tert-butyl alcohol to produce tert-butyl chloride via SN1 reaction.
R3COH > R2CHOH > RCH2OH > CH3OH
Tertiary alcohols react readily with HX alone to form alkyl halide, while secondary and primary require catalyse in the halo hydrogenation reaction. Zinc Chloride acts as the catalyst in the reaction. In some condition, heat supply is needed in the reaction.
Alkyl halide can be prepared from alcohol by reacting them with a hydrogen halide, HX (X=Cl,Br, or I). The mechanism of acid catalyzed substitution of alcohols are termed SN1 and SN2, where “S” stands for substitution while sub-“N” stands for nucleophilic, and the number “1” and “2” is described as first order and second order respectively. The “1” or “2” is also represent the reaction is unimolecular or bimolecular reaction. The secondary alcohols are more favor to react with hydrogen halides by both SN1 and SN2 mechanisms. For primary or methyl alcohol, both molecules undergo SN1 mechanism while tertiary alcohol undergoes SN2 mechanism.
The mechanism of this SN1 reaction involves three steps. First, is the rapid protonation of the alcohol, and then by the much slower rate-determining step, the loss of water to give a relatively stable tertiary carbocation. In the final step, the carbocation is rapidly attacked by...