Organic Chemistry Final

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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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Delta G must be (+ or -) for a reaction to occur
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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

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