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CHM231 Ch.9

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Question
Answer
What's the chemical formula for benzene?   C6H6  
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What are the bond angles in benzene?   All of them are 120 degrees  
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What are the carbon-carbon bond lengths in benzene?   1.39 Angstroms  
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What is the hybridization of each carbon in benzene?   sp2  
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Can the structure of benzene be described correctly using Lewis structures?   No  
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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  
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How does delocalization of pi electrons affect the total energy of a benzene molecule?   It lowers the total energy  
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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  
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What's one way to estimate the resonance energy of benzene?   Compare the heat of hydrogenation of benzene and cyclohexene  
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Is the resonance energy of 1,3 Butadeine smaller or larger than Benzene?   Smaller  
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What's the relation between number of resonance structures and stability of a molecule?   As # resonance structures increases, stability increases  
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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  
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What's a heterocyclic compound?   A compound that contains one or more atoms other than carbon in its ring  
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What's a heterocyclic aromatic compound?   A heterocyclic compound whose ring is aromatic  
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What are two examples of heterocyclic aromatic compounds?   Pyridine (contains 1 N) & pyrimidine (contains 2 N's)  
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What is the hybridization of the Nitrogen atom in pyridine?   sp2  
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What are some examples of aromatic five-membered rings?   Furan, pyrrole, & imidazole  
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What's an electrophilic aromatic substitution?   A reaction in which an electrophile, E+, substitutes for an H on an aromatic ring  
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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  
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How many transition states are there in electrophilic aromatic substitutions?   2  
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What is needed for Chlorine & Bromine to react with benzene, and why?   A catalyst; It increases electrophilicity of the halogen  
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What's a benzene ring connected to an NO2 group called?   A nitrobenzene  
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What does Friedel-Crafts Alkylation do?   It forms a new C-C bond between an aromatic ring and an alkyl group  
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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  
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What are the three locations on a benzene ring in relation to one X-group connected to the ring?   Ortho, meta, para  
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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  
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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  
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What are examples of ortho-para directing & activating groups?   Alkyl groups, phenyl groups, & amines  
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What are examples of ortho-para directing & deactivating groups?   Halogens  
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What are examples of meta-directing & deactivating groups?   Nitro groups, aldehyde groups, & esther groups  
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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  
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What's a phenol?   A 6-carbon ring that is connected to an -OH group  
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Are phenols or alcohols more acidic?   Phenols  
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Is benzene affected by strong oxidizing agents?   No  
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