Organic Chemistry Final – Flashcards
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| Alkyne has a BLANK bond |
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| Triple |
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| Alkene has a BLANK bond |
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| Double |
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| Alkyne + H2 & metal (Pt or Pd) |
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| Triple bond becomes single bond |
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| Alkyne + H2 + Lindlar's catalyst |
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| Triple bond becomes cis double bond |
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| Alkyne + H2 + Ni2B |
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| Triple bond becomes cis double bond |
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| Alkyne + Na2 & NH3 (l) |
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| Triple bond becomes trans double bond |
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| A more stable base corresponds with a BLANK acid |
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| Strong |
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| A more stable base means that the base is BLANK (strong or weak) |
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| Weak |
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| A BLANK (strong or weak) base will deprotonate a terminal alkyne |
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| Strong |
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| A BLANK (strong or weak) base will not deprotonate a terminal alkyne |
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| Weak |
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| Alkyne + H2SO4, H2O, & HgSO4 |
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| Triple bond becomes a single bond and double bonded oxygen on the more substituted position |
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| Alkyne + excess (xs) HX |
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| Triple bond becomes a single bond with two Xs bonded to the more substituted position |
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| Alkyne + HX |
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| Triple bond becomes a double bond with X bonded to the more substituted hindered side |
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| Alkyne + xs X2 & CCl4 |
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| Triple bond becomes a single bond with 2 X's bonded at each end (total of 4) |
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| Alkyne + RX (Ex: MeI) |
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| R is added to to open side of triple bond |
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| Alkyne + 9-BBN, H2O2 & NaOH |
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| Triple bond becomes a single bond and a double bonded O at the less substituted position |
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| Alkyne + Disiamylborane, H2O2, and NaOH |
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| Triple bond becomes a single bond and a double bonded oxygen on the less substituted side |
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| Alkyne + O3 & H2O |
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| Oxidative cleavage: Triple bond becomes a double bonded oxygen and a single bonded OH x2 for each new molecule |
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| Terminal alkyne + O3 &H2O |
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| Oxidative cleavage: Triple bond becomes a double bonded oxygen and a single bonded OH, and CO2 |
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| Enol |
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| Molecule with a C=C double bond alyllically located to an alcohol; very stable |
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| Ketone |
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| Oxygen double bonded to a carbon with an R on each side (resonance-stabilized enol) |
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| Aldehyde |
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| An oxygen double bonded to a carbon with an H on one side and an R on the other |
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| Alkyne + X2 & CCl4 |
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| Triple bond becomes a double bond with an X bonded to each side (trans) |
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| Internal alkyne + NaNH2, NH3 (l) and H2O |
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| Terminal alkyne |
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| Vinylic position |
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| One of the carbons in a C=C double bond |
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| Allylic position |
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| Attached to one of the carbons in a C=C double bond |
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| Hydrogen abstraction |
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| A form of radical inhibition in which hydroquinone donates a hydrogen to destroy a radical and resonance stabilizes itself and then destroys another radical by donating a hydrogen again |
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| Hydrogen abstraction |
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| A form of radical inhibition in which hydroquinone donates a hydrogen to destroy a radical and resonance stabilizes itself and then destroys another radical by donating a hydrogen again |
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| delta H must be (+ or -) for the halogenation of an alkane |
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| - |
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| Delta G must be (+ or -) for a reaction to occur |
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| - |
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| Which is a slower process, bromination or chlorination? And why? |
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| Bromination due to a higher activation energy |
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| When an alkane is chorinated, the Cl is attached at the BLANK position |
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| 60% the more substituted position, 40% the less substituted position |
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| When an alkane is brominated, the Br is attached at the BLANK position |
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| More substituted position |
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| How to determine acid/base strength |
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| ARIO |
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| Pattern of base stability in the periodic table |
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| Increasing to the right, increasing as you go down |
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| Induction effects on base strength |
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| Weaker/stabler when negative atoms provide inductive effects |
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| A negative charge on a triple bond is more or less stable than on a single bond? |
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| More stable |
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| Which is a weaker base, methyl oxide or ethyl oxide? And why? |
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| Methyl oxide because methyl donates less electrons to the oxygen than ethyl |
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| Z designates the top priority atoms to be on the (same or opposite) side(s) of a double bond |
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| Same |
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| E designates the top priority atoms to be on the (same or opposite) side(s) of a double bond |
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| Opposite |
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| Cis double bonds are more or less stable than trans? |
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| Less |
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| Alkene stability can be determined by |
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| The number of substiuents on the double bond |
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| Mechanism for primary carbocation treated with a nucleophile |
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| SN2 |
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| Mechanism for secondary carbocation treated with a nucleophile |
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| SN2 & SN1 |
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| Mechanism for tertiary carbocation treated with a nucleophile |
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| SN1 |
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| Mechanism for a primary carbocation treated with a strong base |
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| E2 |
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| Mechanism for a secondary carbocation treated with a strong base |
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| E2 |
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| Mechanism for a tertiary carbocation treated with a strong base |
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| E2 |
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| Mechanism for a primary carbocation treated with a strong nucleophile/strong base |
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| SN2 (and minor E2) |
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| Mechanism for a secondary carbocation treated with a strong nucleophile/strong base |
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| E2 (and minor SN2) |
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| Mechanism for a tertiary carbocation treated with a strong nucleophile/strong base |
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| E2 |
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| Mechanism for a primary carbocation treated with a weak nucleophile/weak base |
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| N/A |
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| Mechanism for a secondary carbocation treated with a weak nucleophile/weak base |
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| N/A |
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| Mechanism for a tertiary carbocation treated with a weak nucleophile/weak base |
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| SN1 and E1 (high temperature favors E1) |
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| Reagents that are nucleophile only (7) |
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| Cl-,Br-,I-, HS-,H2S, RS-,RSH |
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| Cl-,Br-,I-, HS-,H2S, RS-,RSH |
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| Reagents that are nucleophile only |
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| Reagents that are base only (3) |
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| H-,DBN, DBU |
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| H-,DBN, DBU |
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| Reagents that are base only |
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| Reagents that are strong nucleophiles/strong bases (4) |
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| OH-, MeO-, EtO-, T-BuOK |
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| OH-, MeO-, EtO-, T-BuOK |
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| Reagents that are strong nucleophiles/strong bases |
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| Reagents that act as weak nucleophiles/weak bases (3) |
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| H2O, MeOH, and EtOH |
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| H2O, MeOH, and EtOH |
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| Reagents that act as weak nucleophiles/weak bases |
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| Configuration of SN2 |
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| Inversion (back-side attack) |
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| Rate of SN2 |
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| =k[substrate][nucleophile] |
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| Which is concerted, SN2 or SN1? |
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| SN2 |
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| Carbocation reactivity of SN2 |
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| Primary > Tertiary |
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| Configuration of SN1 |
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| Racemic mixture of inversion and retention |
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| Reactivity of SN1 |
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| Tertiary > Primary |
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| (z) |
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| High priority groups on the same side of a double bond |
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| (e) |
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| High priority groups on opposite sides of a double bond |
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| Is cis more or less stable than trans |
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| More stable |
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| Reactivity of E2 |
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| Tertiary > Primary |
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| E2 mechanism: Double bond in more or less substituted position? |
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| With reagents that are not sterically hindered (OH, MeO, and EtO) the double bond is placed in the more substituted position. With t-BuOK, the double bond is placed in the less substituted position. |
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| Reactivity of E1 |
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| Tertiary > Primary |
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| E1 mechanism: Double bond in more or less substituted position? |
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| Major product is always the more substituted position |
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| Alkene + HX |
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| Double bond becomes single bond with X bonded to the more substituted position |
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| Alkene + HX & ROOR |
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| Double bond becomes single bond with X bonded to the less substituted position |
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| Markovinikov position |
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| X placed in more substituted position |
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| Anti-Markovnikov position |
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| X placed in less substituted position |
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| Zaitsev product |
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| Double bond formed in more substituted position |
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| Hofmann product |
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| Double bond formed in less substituted position |
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| Configuration/stereochemistry of HX addition to an alkene |
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| Racemic mixture of R and S |
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| Alkene + H3O+ |
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| Double bond becomes a single bond and an OH is bonded to the more substituted side |
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| Stereochemistry (configuration) of acid-catalyzed hydration |
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| Racemic mixture of R & S |
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| Difference between acid-catalyzed hydration and oxymercation-demurcation? |
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| Acid catalyzed hydration can undergo carbocation rearrangements, while oxymercation-demurcation cannot |
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| Alkene + Hg(OAc)2, H2O, & NaBH4 |
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| Double bond becomes a single bond and an OH is bonded to the more substituted position (with no rearrangement!) |
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| Alkene + BH3*THF & H2O2, NaOH |
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| Double bond becomes a single bond with an OH bonded to the less substituted position (with no carbocation rearrangement!) |
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| Syn addition |
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| Two atoms are added to the same side of a molecule (dashed and dashed, or wedge and wedge) |
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| Anti addition |
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| Two atoms are added to opposite sides of a molecule (dashed and wedge) |
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| Is hydroboration-oxidation (BH3, THF, H2O2, NaOH) syn or anti? |
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| Syn |
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| Alkene + H2 & Pt |
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| Double bond becomes a single bond |
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| Is catalytic hydrogenation syn or anti? |
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| Syn |
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| Alkene + H2 & Wilkinson's catalyst |
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| Double bond becomes a single bond with syn addition of H's |
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| Alkene + H2 & BINAP |
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| Double bond becomes a single bond with anti addition of H's |
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| Alkene + X2 |
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| Double bond becomes a single bond with an anti addition of an X on each side |
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| Does halogenation (X2) occur via syn or anti addition? |
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| Anti |
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| Alkene + X2 & H2O |
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| Double bond becomes a single bond and an OH is placed at the more substituted position and an X is placed at the other side (anti-addition) |
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| Does halohydrin formation occur via syn or anti addition? |
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| Anti |
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| Alkene + MCPBA & H3O+ |
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| Double bond becomes a single bond with an anti addition of OH on each side |
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| Alkene + OsO4, NaHSO3 & H2O |
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| Double bond becomes a single bond with a syn addition of OH on each side |
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| Alkene + KnO4, NaOH & cold |
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| Double bond becomes a single bond with a syn addition of OH on each side |
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| Alkene + O3 & DMS |
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| Double bond is cleaved into two C=O double bonds |
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| Use of TsCl & Py? |
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| Reagents used before an EN1 reaction if the leaving group is an OH |
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| How to convert an alkene to an alkyne |
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| 1) Br2, CCl4 2) xs NaNH2, H2O |
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| Lowest energy conformation of cyclohexane |
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| Chair |
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| Highest energy conformation of cyclohexane |
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| Half-chair |
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| Second highest energy conformation of cyclohexane |
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| Boat |
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| Second lowest energy conformation of cyclohexane |
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| Twist-boat |
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| Which substituent is more stable: axial or equatorial? |
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| Equatorial |
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| Gauche interaction |
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| A form of steric hinderance present in a staggered conformation |
