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1,3-ciclohexadienă

1,3-ciclohexadienă
Identificare
SMILES
Număr CAS592-57-4
PubChem CID11605
Formulă chimicăC₆H₈[1]  Modificați la Wikidata
Masă molară80,063 u.a.m.[2]  Modificați la Wikidata
Proprietăți
Densitate0,841 g/cm³  Modificați la Wikidata
Punct de topire−89 °C[3]  Modificați la Wikidata
Punct de fierbere80 °C  Modificați la Wikidata
Sunt folosite unitățile SI și condițiile de temperatură și presiune normale dacă nu s-a specificat altfel.
Modifică date / text Consultați documentația formatului

1,3-ciclohexadiena (denumită și benzan) este un compus organic cu formula chimică (C2H4)(CH)4. Este un lichid incolor și inflamabil. Indicele său de refracție este de 1,475 (20 °C, D). Un derivat natural al ciclohexa-1,3-dienei este terpinenul, care este o componentă a uleiului de pin.

Obținere

Ciclohexadiena se prepară prin dehidrobromurarea trans-1,2-dibromociclohexanului,[4] obținut prin bromurarea ciclohexenei:[5]

În general, 1,3-ciclohexadienele pot fi obținute prin reacții de ciclizare a 1,3,5-hexatrienelor.[6]

Proprietăți

Comparativ cu izomerul său, 1,4-ciclohexadiena, ciclohexa-1,3-diena este cu aproximativ 1,6 kJ/mol mai stabilă.[7]

Structura 1,3-ciclohexadienei

Reacțiile chimice utile ale acestei diene ciclice sunt cicloadițiile, cum ar fi reacția Diels-Alder.

Ciclohexadiena și derivații săi formează complecși metal-alchene. Un exemplu este [(C6H8)Fe(CO)3], un lichid portocaliu. Acest complex reacționează cu reactivi de care preiau hidrură, dând derivatul ciclohexadienilic [(C6H7)Fe(CO)3]+.[8]

Note

  1. ^ a b „1,3-ciclohexadienă”, 1,3-CYCLOHEXADIENE (în engleză), PubChem, accesat în  
  2. ^ „1,3-ciclohexadienă”, 1,3-CYCLOHEXADIENE (în engleză), PubChem, accesat în  
  3. ^ Jean-Claude Bradley Open Melting Point Dataset 
  4. ^ Schaefer, John P.; Endres, Leland (). „1,3-Cyclohexadiene”. Organic Syntheses. 47: 31. doi:10.15227/orgsyn.047.0031. 
  5. ^ [1,3-ciclohexadienă pe Google Books Organische Chemie] Verificați valoarea |url= (ajutor). Harri Deutsch Verlag. . p. 135. ISBN 978381711732-1. 
  6. ^ [1,3-ciclohexadienă pe Google Books Organische Chemie: Grundlagen, Verbindungsklassen, Reaktionen, Konzepte ..] Verificați valoarea |url= (ajutor). Georg Thieme Verlag. . p. 121. ISBN 313159987-1. 
  7. ^ NIST Chemistry WebBook 1,4-Cyclohexadiene
  8. ^ Pearson, Anthony J.; Sun, Huikai (). „Cyclohexadieneiron Tricarbonyl”. E-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn00791. ISBN 978-0471936237. 

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