AS.030.205 Chapter Notes - Chapter 18: Acylation, Carbocation, Hydrogenation

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Chapter 18: Reactions of Benzene and Substituted Benzenes

*benzene is an aromatic compound that can be represented by

two resonance contributors

*aromatic compounds are unusually stable

*a compound must be cyclic and planar and have an

uninterrupted cloud of pi electrons above and below the

plane of the molecule; the pi cloud must contain an odd number of pairs of pi

electrons

18.1: The Nomenclature of Monosubstituted Benzenes

Phenyl group: when a benzene ring is a substituent

Benzyl group: a benzene ring with a methylene group

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*with the exception of toluene, benzene rings with an alkyl substituent are named as alkyl-

substituted benzenes (when the alkyl substituent has a name), or as phenyl-

substituted alkanes (when the alkyl substituent does not have a name)

*Aryl (Ar) is the general term for either a phenyl group or a substituted phenyl group, just

as alkyl (R) is the general term for a group derived from an alkane

*ArOH can be used to designate any of the following phenols

18.2: The General Mechanism for Electrophilic Aromatic Substitution Reactions

Electrophilic aromatic substitution reaction: an electrophile substitutes for a hydrogen

that is attached to a ring carbon of an aromatic compound

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*the first step is relatively slow and endergonic b/c an aromatic compound is being

converted to a much less stable nonaromatic intermediate

*the second step is fast and strongly exergonic b/c this step restores the stability-

enhancing aromaticity

18.3: Halogenation of Benzene

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Document Summary

Chapter 18: reactions of benzene and substituted benzenes. *benzene is an aromatic compound that can be represented by two resonance contributors. *a compound must be cyclic and planar and have an uninterrupted cloud of pi electrons above and below the plane of the molecule; the pi cloud must contain an odd number of pairs of pi electrons. Phenyl group: when a benzene ring is a substituent. Benzyl group: a benzene ring with a methylene group. *with the exception of toluene, benzene rings with an alkyl substituent are named as alkyl- substituted benzenes (when the alkyl substituent has a name), or as phenyl- substituted alkanes (when the alkyl substituent does not have a name) *aryl (ar) is the general term for either a phenyl group or a substituted phenyl group, just as alkyl (r) is the general term for a group derived from an alkane. *aroh can be used to designate any of the following phenols.

Related Questions

Classify each of the following statements as true or false:

a) To be classified as organic, a compound must be or have been part of a living organism.

b) Carbon atoms normally form four bonds in organic compounds.

c) Only an unsaturated hydrocarbon can engage in an addition reaction.

d) Members of a homologous series differ by a distinct structural unit.

e) Alkanes, alkenes, and alkynes are unsaturated hydrocarbons.

f) Alkyl groups are a class of organic compounds.

g) Isomers have the same molecular formulas but different structural formulas.

h) Cis-trans isomerism appear among alkenes but not alkynes.

i) All aliphatic hydrocarbons are unsaturated.

j) Aromatic hydrocarbons have a ring structure.

k) An alcohol has an alkyl group bonded to an oxygen atom, and an ether has two.

l) Carbonyl groups are found in alcohols and aldehydes.

m) An ester is an aromatic carbon made from the reaction of an alcohol and a carboxylic acid.

n) An amine has one, two, or three alkyl groups substituted for hydrogens in an ammonia molecule.

o) An amide has the structure of a carboxylic acid except that replaces OH in the carboxyl group.

p) A peptide linkage series arises when a water molecule forms from a hydrogen from the of one amino acid molecule an from an another amino acid molecule.

r) Chain-growth polymers are made a reaction that gives off water a second product.

s) Nylon is an example of a step-growth condensation polymer.

sangriacicada137

For each of the following, fill in the blank with the correct response. All of these fill-in-the-blank problems pertain to material covered in the sections on alkanes, alkenes and alkynes, aromatic hydrocarbons, and hydrocarbon derivatives.

a. The first "organic" compound to be synthesized in the laboratory, rather than being isolated from nature, was _ _ _ _ _, which was prepared from _ _ _ _ _.

b. An organic compound whose carbon-carbon bonds are all single bonds is said to be _ _ _ _ _.

c. The general orientation of the four pairs of electrons around the carbon atoms in alkanes is _ _ _ _ _.

d. Alkanes in which the carbon atoms form a single unbranched chain are said to be _ _ _ _ _ alkanes.

e. Structural isomerism occurs when two molecules have the same number of each type of atom but exhibit a different arrangement of the _ _ _ _ _ between those atoms.

f. The systematic names of all saturated hydrocarbons have the ending _ _ _ _ _ added to a root name that indicates the number of carbon atoms in the molecule.

g. For branched hydrocarbon, the root name for the hydrocarbon comes from the number of carbon atoms in the _ _ _ _ _ continuous chain in the molecule.

h. The positions of substituents along the hydrocarbon framework of a molecule are indicated by the _ _ _ _ _ of the carbon atom to which the substituents are attached.

i. The major use of alkanes has been in _ _ _ _ _ reactions, as a source of heat and light.

j. With very reactive agents, such as the halogen elements, alkanes undergo _ _ _ _ _ reactions, whereby a new atom replaces one or more hydrogen atoms of the alkane.

k. Alkenes and alkynes are characterized by their ability to undergo rapid, complete _ _ _ _ _ reactions, by which other atoms attach themselves to the carbon atoms of the double or triple bond.

l. Unsaturated fats may be converted to saturated fats by the process of _ _ _ _ _.

m. Benzene is the parent member of the group of hydrocarbons called _ _ _ _ _ hydrocarbons.

n. An atom or group of atoms that imparts new and characteristic properties to an organic molecule is called a _ _ _ _ _ group.

o. A _ _ _ _ _ alcohol is one in which there is only one hydrocarbon group attached to the carbon atom holding the hydroxyl group.

p. The simplest alcohol, methanol, prepared industrially by the hydrogenation of _ _ _ _ _.

q. Ethanol is commonly prepared by the _ _ _ _ _ of certain sugars by yeast.

r. Both aldehydes and ketones contain the _ _ _ _ _ group, but they differ in where this group occurs along the hydrocarbon chain.

s. Aldehydes and ketones can be prepared by _ _ _ _ _ of the corresponding alcohol.

t. Organic acids, which contain the _ _ _ _ _ group, are typically weak acids.

u. The typical sweet-smelling compounds called _ _ _ _ _ result from the condensation reaction of organic acid with an _ _ _ _ _.

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AS.030.205 Chapter Notes - Chapter 18: Acylation, Carbocation, Hydrogenation

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