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OCHEM FINAL EXAM
| BLANK | ANSWER |
|---|---|
| In the dienophile, the ____ is raised by the addition of electron ___________ groups | HOMO, withdrawing |
| In the diene, the LOMO is _______ by the addition of electron _______ groups | Lowered, donating |
| In the allyl radical, the nonbonding orbital (SOMO) is (in phase/out of phase) | Out of phase |
| If there are 3 atomic orbitals, there are _ molecular orbitals | 3 |
| The HOMO is always (in phase/out of phase) | In phase |
| A conjugated system is (more/less) stable than an unconjugated system | more |
| Energy required to jump 1 electron 1 orbital | HOMO-LUMO gap |
| A molecule absorbs the (same/opposite) color that it emits | opposite |
| In nucleophilic attack of dienes, the two possible additions are denoted as __, __. The more stable form (thermodynamic form) is __, while the other is kinetic. | 1,4; 1,2; 1,4 |
| Raising the HOMO gap and lowering the LUMO gap is important in the dies-alder reaction because it lowers the ___________, making the addition easier | HOMO-LUMO gap |
| Dienophiles are activated by _________________ groups | Electron withdrawing |
| Dienes are activated by _______________ groups | Electron donating |
| Dies Alder is a (syn/anti) addition | syn |
| In electrophilic aromatic substitution, the ________ of the ________ ____ is replaced by the electrophile | Hydrogen, aromatic ring |
| Halogenation: aromatic ring + ___ | X2, FeX3 |
| Nitration: aromatic ring + ____ | HNO3, H2SO4 |
| Sulfonation: aromatic ring + ____ | SO3, H2SO4 |
| Friedel-Crafts Alkylation: aromatic ring + ____. In place of the alkyl halide, ____ can be used | RCl, AlCl3, catalytic acid |
| Friedel-Crafts Acylation: aromatic ring + ____ | RCOCl, AlCl3 |
| The rate determining step of electrophilic aromatic substitution is the _____, and the fastest step is the ________ | Nucleophilic attack by aromatic ring, regeneration of aromatic ring |
| Which cannot be used for the Friedel-Crafts Alkylation as an acid? FeX3, AlCl3, BF4, BF3, ZrCl4 | BF4 |
| The Friedel-Crafts Alkylation does not work if electron ________ groups are on the ring. It is faster if _____ substituents are on the ring. | Withdrawing, alkyl |
| The Friedel-Crafts Acylation does not work if a ___________ is on the ring | substituent |
| Clemmensen Reduction: aromatic ring with carbonyl + Zn(Hg) in HCl yield ___ | Aromatic ring without carbonyl |
| Wolff-Kishner Reduction: aromatic ring with carbonyl + hydrazine, KOH yields | Aromatic ring without carbonyl |
| Electron donating substituents are __ directing | o/p |
| Electron withdrawing substituents are __ directing | m |
| Benzylic halogenation: toluene + Cl2 yields (mono/polychlorinated) | polychlorinated |
| H2, metal; Fe, acid, EtOH, H2O | Reducers |
| Fe, acid, EtOH, H2O; KMnO4, OH-, H+; H2Cr2O4 | Oxidators |
| Birch reduction dissolves metal to ______ aromatic rings to 1.4-cyclohexadienes using a mixture of ____________ | Reduce, ammonia and alcohol |