Second substituent

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Second substituents ( marked in green ) on the benzene ring. The yields given are relative yields of the substitution reaction.
Nitrotoluene Synthesis.svg
A green marked nitro group as a second substituent on the benzene ring.
Toluene sulfonic acid Synthesis.svg
A green sulfonic acid group as a second substituent on the benzene ring.
Chloro nitrobenzene Synthesis.svg
A green marked nitro group as a second substituent on the benzene ring.
Dinitrobenzene Synthesis.svg
A green marked nitro group as a second substituent on the benzene ring.

A Zweitsubstituent is in the organic chemistry of the second substituent on an aromatics (mostly derived from benzene ). The originally unsubstituted aromatic is monosubstituted after the occurrence of the first substituent and disubstituted after the occurrence of the second substituent. If you subject z. B. a monosubstituted benzene derivative of an electrophilic substitution , the newly occurring second substituent can be in the ortho , meta or para position relative to the first substituent. At the same time, the reaction rate of the electrophilic second substitution of the monosubstituted benzene can be greater or less than that of benzene, depending on the nature of the first substituent.

Individual evidence

  1. Joachim Buddrus, Bernd Schmidt: Basics of Organic Chemistry , 5th edition, de Gruyter Verlag, Berlin, 2015, pp. 402–404, ISBN 978-3-11-030559-3 .
  2. Peter Sykes: Reaction Mechanisms of Organic Chemistry VCH, 9th revised edition, 1988, pp. 172-188, ISBN 3-527-26872-3 .
  3. ^ Ulrich Lüning: Organic reactions , 2nd edition, Elsevier GmbH, Munich, 2007, pp. 86–89, ISBN 978-3-8274-1834-0 .