Organic Chemistry Final

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

Get help with your homework


image
Haven't found the Essay You Want? Get your custom essay sample For Only $13.90/page

Sarah from studyhippoHi there, would you like to get such a paper? How about receiving a customized one?

Check it out