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Chemistry · Ch 14 — Basic Principles of Organic Chemistry

Types of reagent

14.6.2

Types of reagent

Organic reagents are classified into two broad types, based purely on whether they DONATE or ACCEPT electrons when they react with a substrate. A polyatomic ELECTROPHILE (literally, 'electron-loving') is a species that carries an electron-DEFICIENT atom somewhere within it -- that particular atom is called its electrophilic centre. A polyatomic NUCLEOPHILE (literally, 'nucleus-seeking') instead carries an electron-RICH atom somewhere within it -- that atom is called its nucleophilic centre. For instance, in the electrophile AlCl3AlCl_3, the electrophilic centre is the aluminium atom itself, since it has only six valence electrons around it (an incomplete octet, leaving it genuinely electron-hungry); in the nucleophile H2OH_2O, the nucleophilic centre is the oxygen atom, since it carries two full lone pairs of electrons it can potentially donate. When a reaction actually happens between the two, a NUCLEOPHILE attacks the electrophilic centre present in a substrate, bringing about what is called a nucleophilic reaction; conversely, an ELECTROPHILE attacks the nucleophilic centre present in a substrate, bringing about what is called an electrophilic reaction. This general principle is illustrated (using a simple, technically inorganic example, purely to demonstrate the idea cleanly) by ammonia reacting with boron trifluoride: NH3+BF3→H3N−BF3NH_3 + BF_3 \rightarrow H_3N{-}BF_3, in which ammonia's nitrogen lone pair (the nucleophilic centre in NH3NH_3) attacks boron (the electrophilic centre in BF3BF_3, which has only six valence electrons around it) to form the product. Within genuinely POLAR organic reactions specifically, this same electrophile/nucleophile framework is what actually drives the chemistry: ELECTROPHILES (E⊕E^{\oplus}) are electron-SEEKING species, since they are themselves electron-deficient -- examples include an outright positively-charged ion such as $Br^{\oplus} …

Misc Problem 14.5Identifying the nucleophile and electrophile in NH3 and CH3⊕

Worked out. Worked example. Drawing the full structural formulae with every valence electron shown: NH3 is H-N(H)(H) with one lone pair remaining on N; CH3⊕ is H-C(H)(H) with a positive charge and no lone pair on C. Since NH3's nitrogen carries a lone pair it can donate to another species, NH3 is a nucleophile and N is its nucleophilic centre. Since CH3⊕ is a positively charged, electron-deficient species with a vacant orbital on carbon, it is an electrophile and C is its electrophili …