click below
click below
Normal Size Small Size show me how
Organic Test 2
Term | Definition |
---|---|
What do you do with H3O+, H2O (acid catalyst hydration) (alkene)? | Adds an H and OH in place of the pi-bond. OH is on the most substituted, and carbocation rearrangement is possible. |
1. Hg(OAc)2, H2O 2. NaBH4 Oxymercuration-reduction hydration: alkene | Adds OH and H in place of pi-bond, with OH on most substituted. NO carbocation rearrangement. |
1. BH3 2. H2O2 Hydroboration hydration; alkene | Adds OH and H in place of pi-bond, with OH on least substituted. |
1. OsO4 2. NHSO4 (or Zn) Sin-dihydroxylation; alkene | Adds 2OH in syn (cis) conformation with NO carbocation rearrangement. |
1. O3 2. Zn (or NaSO3) Ozonolysis | Cleaves both the pi and sigma bonds and adds an O to each end via double bonds. |
Addition of X2 | Adds 2X in anti (trans) formation with NO carbocation rearrangement |
X2, H2O | Adds X and OH in anti (trans) conformation, with OH on most substituted. NO carbocation rearrangement |
HX addition | H and X added with X on most substituted. Can have carbocation rearrangement. |
1. NaNH2 (base) 2. Carbon skeleton with X attached | Adds carbon skeleton to alkyne. Only works when alkyne is on end |
1. X2 2. NaNH2 (base) | Changes alkene to alkyne |
HX addition to alkyne | Adds 2H on least sub, and 2X on most sub. Goes from alkyne ->alkane |
X2 addition to alkyne | No stereochemistry needed. 4X added, with 2X on each C. However, like with alkene rxn each 2X is added in anti conformation. |
H2, Pd Alkene | Adds 2H in syn (cis) conformation in place of pi-bond. |
HgSO4; H2O, H3O+ | For alkynes, adds O double bonded to most substituted C. Alkyne -> alkane but with O double bond |
1. HBR2 (BH3) 2. H2O2 | Adds O double bonded to least substituted. |
H2, Pd Alkyne | Saturates alkyne to alkane (adds 4H, 2 on each C) |
H2, Lindler's catalyst | Stops reaction after addition of 2H, making it go alkyne to alkene. Alkene is in CIS/Z conformation (rxn proceeds syn) |
Na, NH3 | Adds 2H (similar to H2, Lindler's catalyst), but resulting alkene is in trans/E conformation. This is more stable. |
Transition state | Is at crest of reaction energy (where activation energy is on potential energy diagram). Resembles either the reactants or products; whichever is closest to it in energy. |
In an exothermic reaction, the transition state will be: | "Early", looks like reactants |
In an endothermic reaction, the transition state will be: | "Late", looks like products |
In free radical bromination (more specific type of halogenation) (addition of Br from Br2 to a carbon skeleton) , the Br will be placed: | On the most substituted C |
Free radical halogenation | Remove an H, replace it with an X. Cl isn't selective, but Br wants to be on most sub. |
Hemolysis | Where 1 e- goes to each atom in a bond |
Initiation step | Beginning of free radical halogenation where more free radicals are created (most often X2 being 2X with each being a free radical) |
Propegation step 1 | 2nd step of free radical halogenation. Where a free radical X joins with an H from carbon skeleton, leaving the carbon skeleton with a free radical where the H was. |
Propegation step 2 | Last step of free radical halogenation. Another molecule of X2 splits, with an X going to bond with free radical of carbon skeleton and the other becoming a free radical. |
Z | Same side |
E | Different side |