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45 Cards in this Set
- Front
- Back
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What does the overall Wheland intermediate look like?
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Draw the 3 resonance forms of Wheland intermediate.
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Draw the overall scheme of SEAr.
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What is the rate determining step of nitration?
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Addition of the nitro group
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What does the energy diagram of nitration look like?
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What does the intermediate of nitration look like?
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When is FeBr3 necessary for bromination and why?
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When the aromatic ring is not activated
It is a Lewis base that will draw some of the electron density to one of the bromines in Br2, making the other δ+, a good electrophile |
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What purpose does AlCl3 serve in chlorination of aromatic compounds?
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Lewis acid, can break bond of Cl2 for non-activating aromatic rings.
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What is the purpose of HNO3/Δ in iodination(?).
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They oxidize the I2 into 2I+, an active electrophile.
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How can a halogenated aromatic compound be used in making a C-C bond?
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Griiiignard. Grigs are strong nucleophiles - add to electrophiles (aldehyde or ketone)
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In sulfonation of benzene, which conditions give a faster reaction?
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SO3/H2SO4 is faster than hot conc. H2SO4
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In sulfonation of benzene, which conditions give a slower reaction?
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Hot conc. H2SO4 is slower than SO3/H2SO4
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Why is MX3 a necessary reagent in Friedel Crafts alkylation?
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It is a Lewis acid that will break the R-X bond
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Which Lewis acid might cause carbocation rearrangements?
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AlCl3
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What Lewis acid might you use to prevent carbocation rearrangement for Friedel Crafts alkylation?
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FeCl3 is one of many
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Draw the general mechanism of Friedel Crafts alkylation
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Which R groups are the best for Fried craft alkylation?
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2° or 3° are best because they are more stable carbocations than 1°
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(FC alkylation)
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(FC alkylation)
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Show how the carbocation rearrangement occurs.
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What does an acylium ion look like?
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How is an acylium ion made during fried craft acylation?
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What are the two advantages of FC acylation over alkylation?
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There are no carbocation rearrangements, and there is no issue with polyalkylation.
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NOT THE ONLY ANSWER DUDE. WHATEVER RELAX
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What are some substituents that are deactivating?
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Halogens, and electron withdrawing groups
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Which substituents are deactivating and o/p directing?
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Halogens
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What are some substituents that are strongly o/p directing?
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-OH, -OR, -NH2, -NR2
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Where do these guys direct other substituents in SEAr?
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o/p
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Why are halogens o/p directing? Shouldn't they be greedy electron sucking ***?
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They are indeed electron withdrawing through induction, but they also donate their electrons through their lone pairs.
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