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CHM231 Ch.9

What's the chemical formula for benzene? C6H6
What are the bond angles in benzene? All of them are 120 degrees
What are the carbon-carbon bond lengths in benzene? 1.39 Angstroms
What is the hybridization of each carbon in benzene? sp2
Can the structure of benzene be described correctly using Lewis structures? No
What's resonance? The concept in which two or more equivalent Lewis structures for the same arrangement of atoms (resonance structures) are necessary to describe the bonding
How does delocalization of pi electrons affect the total energy of a benzene molecule? It lowers the total energy
What's resonance energy? The difference in energy between a resonance hybrid with delocalized pi electrons and its most stable hypothetical contributing structures in which electrons are localized
What's one way to estimate the resonance energy of benzene? Compare the heat of hydrogenation of benzene and cyclohexene
Is the resonance energy of 1,3 Butadeine smaller or larger than Benzene? Smaller
What's the relation between number of resonance structures and stability of a molecule? As # resonance structures increases, stability increases
What properties must a ring have to be considered aromatic? Have 1 2p orbital on each atom of the ring, be planar or nearly planar, & have 4n+2 pi electrons in the cyclic arrangement of 2p orbitals
What's a heterocyclic compound? A compound that contains one or more atoms other than carbon in its ring
What's a heterocyclic aromatic compound? A heterocyclic compound whose ring is aromatic
What are two examples of heterocyclic aromatic compounds? Pyridine (contains 1 N) & pyrimidine (contains 2 N's)
What is the hybridization of the Nitrogen atom in pyridine? sp2
What are some examples of aromatic five-membered rings? Furan, pyrrole, & imidazole
What's an electrophilic aromatic substitution? A reaction in which an electrophile, E+, substitutes for an H on an aromatic ring
What's the steps for an electrophilic aromatic substitution? A reagent generates an electrophile; Electrophile reacts with the ring; Finally a proton transfer occurs & regenerates the aromatic ring
How many transition states are there in electrophilic aromatic substitutions? 2
What is needed for Chlorine & Bromine to react with benzene, and why? A catalyst; It increases electrophilicity of the halogen
What's a benzene ring connected to an NO2 group called? A nitrobenzene
What does Friedel-Crafts Alkylation do? It forms a new C-C bond between an aromatic ring and an alkyl group
What's an acid chloride and what's another name for it? Acyl chloride; It's a derivative of a carboxylic acid in which the -OH is replaced by a chlorine
What are the three locations on a benzene ring in relation to one X-group connected to the ring? Ortho, meta, para
What is the name of a subsituent that causes the rate of a second substitutent to be greater than that of benzene itself? Activating substituent
What is the name of a subsituent that causes the rate of a second substitutent to be lower than that of benzene itself? Deactivating substituent
What are examples of ortho-para directing & activating groups? Alkyl groups, phenyl groups, & amines
What are examples of ortho-para directing & deactivating groups? Halogens
What are examples of meta-directing & deactivating groups? Nitro groups, aldehyde groups, & esther groups
When the second substituent is in ortho or para positions compared to meta positions, is there a better or worse resonance stabilization of the carbocation intermediate? Better
What's a phenol? A 6-carbon ring that is connected to an -OH group
Are phenols or alcohols more acidic? Phenols
Is benzene affected by strong oxidizing agents? No
Created by: 817229501