Friday, August 22, 2014

What is the product of 2-chloro-2-methylpropane and sodium hydrogen carbonate?

Sodium hydrogen carbonate is the Internation Union of Pure and Applied Chemistry (IUPAC) name for the compound more commonly known as sodium bicarbonate (baking soda). The chemical formula for this compound is NaHCO3.


2-chloro-2-methylpropane is the IUPAC name for tert-Butyl chloride, an organic compound with 4 carbons. It is so named because a chain of 3 carbons is called propane. The carbons are labeled in order, so substituents in the 2- position would be bonded to the middle carbon in the 3 carbon chain. 


Sodium bicarbonate is a weak base and will not react with tert-Butyl chloride. These compounds are typically found in a standard organic chemistry synthesis of tert-Butyl chloride from tert-Butanol (2-methyl-2-propanol). This reaction occurs in the presence of a strong acid, hydrochloric acid (HCl). The HCl protonates the oxygen in the alcohol group. Following the loss of a water molecule, the carbocation (in the 2-position) reacts with the chloride ion in a substitution nucleophilic unimolecular (SN1) reaction. Because this reaction requires HCl, sodium bicarbonate is added to neutralize the acid. Sodium bicarbonate is utilized precisely because it will not react with the tert-Butyl chloride. 

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