Welcome to Wikipedia



Download 190.74 Kb.
Page3/7
Date19.10.2016
Size190.74 Kb.
#3394
1   2   3   4   5   6   7

See also[edit]


  • Abiogenic petroleum origin

  • Biohydrocarbon

  • Carbohydrates

  • Energy storage

  • Fractional distillation

  • Functional group

  • Hydrocarbon mixtures

  • Hydrocarbons on other planets

  • Organically moderated and cooled reactor

References[edit]


    1. Jump up ^ Silberberg, 620

    2. Jump up ^ IUPAC Goldbook hydrocarbyl groups

    3. Jump up ^ Clayden, J., Greeves, N., et al. (2001) Organic Chemistry Oxford ISBN 0-19-850346-6 p. 21

    4. Jump up ^ McMurry, J. (2000). Organic Chemistry 5th ed. Brooks/Cole: Thomson Learning. ISBN 0-495-11837-0 pp. 75–81

    5. Jump up ^ Silderberg, 623

    6. ^ Jump up to: a b Silderberg, 625

    7. Jump up ^ Silderberg, 627

    8. Jump up ^ Meierhenrich, Uwe. Amino Acids and the Asymmetry of Life. Springer, 2008. ISBN 978-3-540-76885-2

    9. Jump up ^ Silderberg, 628

    10. Jump up ^ Silderberg, 631

    11. Jump up ^ http://www.jpl.nasa.gov/news/news.php?release=2013-364

    12. Jump up ^ http://arxiv.org/abs/1403.1856

    13. Jump up ^ Dan Morgan, Lecture ENVIRO 100, University of Washington, 11/5/08

    14. Jump up ^ Eskandarlou M, Moaddab AH. Chest wall necrosis and empyema resulting from attempting suicide by injection of petroleum into the pleural cavity. Emerg Med J. 2010 Aug;27(8):616-8. doi: 10.1136/emj.2009.073486. Epub 2010 Jun 17.

    15. Jump up ^ World Coal, Coal and Electricity, http://www.worldcoal.org/coal/uses-of-coal/coal-electricity/, retrieved 07/03/2012

    16. Jump up ^ Mason OU, Nakagawa T, Rosner M, Van Nostrand JD, Zhou J, Maruyama A, Fisk MR, Giovannoni SJ. (2010). "First investigation of the microbiology of the deepest layer of ocean crust.". PLoS ONE 5 (11): e15399. doi:10.1371/journal.pone.0015399. PMC 2974637. PMID 21079766.

    17. Jump up ^ M.M. Yakimov, K.N. Timmis & P.N. Golyshin (2007). "Obligate oil-degrading marine bacteria". Curr. Opin. Biotech. 18 (3): 257–266. doi:10.1016/j.copbio.2007.04.006. PMID 17493798.

    18. Jump up ^ Paul Stamets in Mycellium Running, Chapter 7, page 86, Mycoremediation, ISBN 9781580085793, or his TEDx video http://www.ted.com/talks/paul_stamets_on_6_ways_mushrooms_can_save_the_world?language=en

Bibliography[edit]


  • Silberberg, Martin. Chemistry: The Molecular Nature Of Matter and Change. New York: McGraw-Hill Companies, 2004. ISBN 0-07-310169-9

External links[edit]

Aromatic hydrocarbon


From Wikipedia, the free encyclopedia

Jump to: navigation, search



"Arene" redirects here. For other uses, see Arene (disambiguation).

An aromatic hydrocarbon or arene[1] (or sometimes aryl hydrocarbon)[2] is a hydrocarbon with alternating double and single bonds between carbon atoms forming rings. The term 'aromatic' was assigned before the physical mechanism determining aromaticity was discovered; the term was coined as such simply because many of the compounds have a sweet or pleasant odor. The configuration of six carbon atoms in aromatic compounds is known as a benzene ring, after the simplest possible such hydrocarbon, benzene. Aromatic hydrocarbons can be monocyclic (MAH) or polycyclic (PAH).

Some non-benzene-based compounds called heteroarenes, which follow Hückel's rule (for monocyclic rings: when the number of its π-electrons equals 4n+2), are also called as aromatic compounds. In these compounds, at least one carbon atom is replaced by one of the heteroatoms oxygen, nitrogen, or sulfur. Examples of non-benzene compounds with aromatic properties are furan, a heterocyclic compound with a five-membered ring that includes an oxygen atom, and pyridine, a heterocyclic compound with a six-membered ring containing one nitrogen atom.[3]

Contents


[hide]

  • 1 Benzene ring model

  • 2 Arene synthesis

  • 3 Arene reactions

    • 3.1 Aromatic substitution

    • 3.2 Coupling reactions

    • 3.3 Hydrogenation

    • 3.4 Cycloadditions

  • 4 Benzene and derivatives of benzene

  • 5 Polycyclic aromatic hydrocarbons

  • 6 See also

  • 7 References

  • 8 External links

Benzene ring model[edit]


http://upload.wikimedia.org/wikipedia/commons/thumb/0/07/benzene_circle.svg/100px-benzene_circle.svg.png

Benzene


Main article: aromaticity

Benzene, C6H6, is the simplest aromatic hydrocarbon, and it was the first one recognized. The nature of its bonding was first recognized by August Kekulé in the 19th century. Each carbon atom in the hexagonal cycle has four electrons to share. One goes to the hydrogen atom, and one each to the two neighboring carbons. This leaves one to share with one of its two neighboring carbon atoms, which is why the benzene molecule is drawn with alternating single and double bonds around the hexagon.

The structure is also illustrated as a circle around the inside of the ring to show six electrons floating around in delocalized molecular orbitals the size of the ring itself. This also represents the equivalent nature of the six carbon-carbon bonds all of bond order ~1.5. This equivalency is well explained by resonance forms. The electrons are visualized as floating above and below the ring with the electromagnetic fields they generate acting to keep the ring flat.

General properties:



  1. Display aromaticity.

  2. The carbon-hydrogen ratio is high.

  3. They burn with a sooty yellow flame because of the high carbon-hydrogen ratio.

  4. They undergo electrophilic substitution reactions and nucleophilic aromatic substitutions.

The circle symbol for aromaticity was introduced by Sir Robert Robinson and his student James Armit in 1925[4] and popularized starting in 1959 by the Morrison & Boyd textbook on organic chemistry. The proper use of the symbol is debated; it is used to describe any cyclic pi system in some publications, or only those pi systems that obey Hückel's rule on others. Jensen[5] argues that in line with Robinson's original proposal, the use of the circle symbol should be limited to monocyclic 6 pi-electron systems. In this way the circle symbol for a 6c–6e bond can be compared to the Y symbol for a 3c–2e bond.


Download 190.74 Kb.

Share with your friends:
1   2   3   4   5   6   7




The database is protected by copyright ©ininet.org 2024
send message

    Main page