ABSTRACT
There are nucleophiles that are prevalent in biochemical reactions, including alcohols, amines, and thiols. This chapter briefly reviews the SN2 and SN1 reactions and then describes nucleophiles that are common in biochemical applications and the substitution reactions that are common for these nucleophiles. The fundamentals of both acyl addition and of acyl substitution reactions will be presented for carbonyl electrophilic centers and the reactions of these electrophilic centers with nucleophiles. Amines react as nucleophiles with alkyl halides in SN2 reactions, as in the conversion of 1-bromopropane to propane-1-(N,N-dimethylammonium) bromide to N,N-dimethylpropan-1-amine rather than ammonium salt. Epinephrine injection is used for emergency treatment of severe allergic reactions (including anaphylaxis) to insect bites or stings, medicines, foods, etc. In all cases, these nucleophiles are classified as weak nucleophiles, and the initial acyl addition is followed by formation of intermediate products, such as formation a hemiacetal that reacts further to give the final product, an acetal.
