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In this usage, a leaving group is a less formal but more commonly used synonym of the term nucleofuge. In this context, leaving groups are generally anions or neutral species, departing from neutral or cationic substrates, respectively, though in rare cases, cations leaving from a dicationic substrate are also known. [3]
Mesylate esters are a group of organic compounds that share a common functional group with the general structure CH 3 SO 2 O−R, abbreviated MsO−R, where R is an organic substituent. Mesylate is considered a leaving group in nucleophilic substitution reactions. [2]
Tosyl group (blue) with a generic "R" group attached Tosylate group with a generic "R" group attached. Note the extra oxygen, compared to plain tosyl. In organic chemistry, a toluenesulfonyl group (tosyl group, abbreviated Ts or Tos [nb 1]) is a univalent functional group with the chemical formula −SO 2 −C 6 H 4 −CH 3.
A nucleophilic aromatic substitution (S N Ar) is a substitution reaction in organic chemistry in which the nucleophile displaces a good leaving group, such as a halide, on an aromatic ring. Aromatic rings are usually nucleophilic, but some aromatic compounds do undergo nucleophilic substitution.
This means that the better the leaving group, the faster the reaction rate. A general rule for what makes a good leaving group is the weaker the conjugate base, the better the leaving group. In this case, halogens are going to be the best leaving groups, while compounds such as amines, hydrogen, and alkanes are going to be quite poor leaving ...
In order for the S N 2 reaction to take place there must be a good leaving group which is strongly electronegative, commonly a halide. [4] In the Williamson ether reaction there is an alkoxide ion (RO −) which acts as the nucleophile, attacking the electrophilic carbon with the leaving group, which in most cases is an alkyl tosylate or an ...
Weak bases are better leaving groups than strong bases; a species with a strong conjugate acid (e.g. hydrochloric acid) will be a better leaving group than a species with a weak conjugate acid (e.g. acetic acid). Thus, chloride ion is a better leaving group than acetate ion. The reactivity of acyl compounds towards nucleophiles decreases as the ...
The sulfonyl functional group (RS(O) 2 R') has become an important electron-withdrawing group for modern organic chemistry. α-Sulfonyl carbanions may be used as nucleophiles in alkylation reactions, Michael-type additions, and other processes. [3] After having served their synthetic purpose, sulfonyl groups are often removed.