DAT Organic Chemistry
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| As a pure liquid, what makes hydrogen bonds? | F-H, O-H, N-H
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| What could hydrogen bond with something protic like H2O? | F, O, N
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| What is the stability of carbocations? | 3˚>2˚>1˚>Methyl
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| What do electron withdrawing groups do to nucleophiles? | Stabilizes them
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| What do electron withdrawing groups do to electrophiles? | Makes them stronger
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| How can you tell if something is oxidized or reduced? | More Oxygen = Oxidized,
More Hydrogen = Reduced
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| How do you measure units of unsaturation? | CnH2n+2
1˚ for every π bond, or electron pair.
(When N is present, add 1 H to total)
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| How do you rank bases? | CARDIO
Charge, Atom (size, bigger=more stable) Resonance, Dipole Induction, Orbital
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| Are chiral compounds optically active? | No, chiral compounds are not optically active.
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| What is a racemic mixture? | 1/2: 1/2 enantiomer ratio, so it does not rotate light at all.
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| How can you tell if it is an enantiomer or not? | Enantiomers = exact opposites of chiral centers.
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| What is an epimer? | A diastereomer with 1 chiral center that is different.
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| What is a diastereomer? | Some chiral centers match, some do not.
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| Which type of reaction causes inversion of chiral centers? | SN2
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| What are the respective orders of SN1 and SN2 reactions? | SN1 = 1st order rate law
SN2 = 2nd order rate law
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| Which reaction produces a racemization of enantiomers? | SN1
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| What type of electrophiles do SN2 reactions prefer? | CH3 > 1˚ > 2˚
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| What type of electrophiles do SN1 reactions prefer? | 3˚ > 2˚
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| Which reaction prefers a protic solvent? | SN1
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| What type of reaction will a strong base go with? | E2
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| What is the order of electrophiles that E1 reactions prefer? | 3˚ > 2˚
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| What is the order of electrophiles that E2 reactions prefer? | 3˚> 2˚>1˚
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| What is the product of a bulky base + tert butoxide? | The "Hoffman" product - Terminal Alekene
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| Are halogens (-F, -Cl, -Br, -I) activating or deactivating? | Deactivating - but they direct in an Ortho/Para manner.
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| Are π donors (-NH2, -OH, -OR, and -NHCOCH3) activating or deactivating and how do they direct? | Activating - ORTHO/ PARA
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| How do these functional groups direct? -SO3H, -CN, -NO2, -NR3 | META directors because they are "Deactivating"
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| How do carbonyl groups direct? | Meta directors because they are "deactivating"
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| In order to be meso what does a compound have to have? | 1. Chiral centers 2. A plane of symmetry
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