Organic 11: Arenes & Aromaticity Flashcards Preview

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Flashcards in Organic 11: Arenes & Aromaticity Deck (26)
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1
Q

Arenes

A

hydrocarbons based on the benzene ring as a structural unit; ex. benzene, toluene, naphthalene; AKA aromatic hydrocarbons

2
Q

Aromaticity

A

special stability associated with aromatic compounds

3
Q

Aliphatic hydrocarbons

A

alkanes, alkenes, and alkynes belong to this class; name given to hydrocarbons that were obtained by the chemical degradation of fats

4
Q

Kekule (accented final e) structure

A

structural formula for an aromatic compound that satisfies the customary rules of bonding and is usually characterized by a pattern of alternating single and double bonds; two formulations for benzene are 1, 2 and 1, 6 disub’d; a single structure does not completely describe the actual bonding in the molecule

5
Q

Resonance energy

A

extent to which a substance is stabilized by electron delocalization; it is the difference between the substance and a hypothetical model in which the electrons are localized

6
Q

Closed-shell electron configuration

A

stable electron configuration in which all the lowest energy orbitals of an atom (in the case of the noble gases), an ion (e.g. Na+), or a molecule (e.g. benzene) are filled

7
Q

Xylenes

A

dimethyl derivatives of benzene; 3 isomers: ortho-, meta-, and para-

8
Q

Ortho-

A

prefix signifying a 1,2-disubstituted benzene ring

9
Q

Meta-

A

prefix signifying a 1,3-disubstituted benzene ring

10
Q

Para-

A

prefix signifying a 1,4-disubstituted benzene ring

11
Q

Phenyl-

A

when the benzene ring is named as a substituent, this word stands for C6H5-

12
Q

Aryl group

A

an arene named as a substituent

13
Q

Benzyl group

A

C6H5CH2-

14
Q

Polycyclic aromatic hydrocarbons

A

members of this class of arenes possess substantial resonance energies because each is a collection of benzene rings fused together

15
Q

Carcinogen

A

cancer-causing substance; ex. benzo[a]pyrene

16
Q

Buckminsterfullerene

A

name given to the C60 cluster with structure resembling the geodesic domes of R. Buckminster Fuller

17
Q

Electrophilic aromatic substitution

A

most important reaction type exhibited by benzene and its derivatives

18
Q

Benzylic carbon

A

a carbon atom that is directly attached to a benzene ring

19
Q

Birch reductions

A

metal-ammonia-alcohol reductions of aromatic rings

20
Q

Anti-aromatic molecules

A

molecules that are destabilized by delocalization of their pi electrons

21
Q

Huckel’s Rule

A

among planar, monocyclic, fully conjugated polyenes, only those possessing (4n + 2) pi electrons, where n is a whole number, will have special stability, that is, be aromatic

22
Q

Frost Circle

A

a mnemonic that gives the Huckel pi MOs for cyclic conjugated molecules and ions

23
Q

Annulene

A

refers to completely conjugated monocyclic hydrocarbons with more than 6 carbons

24
Q

[x]annulene

A

higher members of the annulene group, where x is the number of carbons in the ring

25
Q

Heterocyclic compounds

A

cyclic compounds that contain at least 1 atom other than carbon within their ring

26
Q

Heterocyclic aromatic compounds

A

cyclic compounds that contain at least 1 atom other than carbon within their ring and possess aromatic stability

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