Term
| as a halide gets bigger, C-X bond length gets ________ and _________; electronegativity therefore ___________ except from C-F to C-Cl where it _____________ |
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Definition
| as a halide gets bigger, C-X bond length gets LONGER and WEAKER; electronegativity therefore DECREASES except from C-F to C-Cl where it INCREASES (slightly) |
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Term
| a tertiary hydrogen is _______ reactive in radical halogenation than a primary because its radical product is __________ stable |
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Definition
| a tertiary hydrogen is MORE reactive in radical halogenation than a primary because its radical product is MORE stable |
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Term
| In radical halogenation, Br will almost exclusively end up on more highly-substituted carbons (more so that Cl) because.... |
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Definition
| Radical bromination is ENDOTHERMIC; because of the Hammond Postulate, this means the TS more closely resembles the intermediate. Therefore, the more stable the intermediate, the more stable the TS and the lower the activation energy. |
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Term
| what is allylic bromination and how do you do it? |
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Definition
| adding bromide to a carbon ONE AWAY from a double bond; it's a radical substitution rection with NBS, light, and CCl4 |
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Term
| why is an allylic carbon going to pick up the Br in allylic bromination? |
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Definition
| its H bond is easiest to break; this is because its radical product is stabilized by resonance structures |
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Term
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Definition
| PBr3 - changes an alcohol to an alkyl halide in ether |
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Term
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Definition
| six-membered aromatic ring with N replacing one of the carbons |
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Term
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Definition
| SOCl2 (S double bonded to O); turns an alcohol into an alkyl halide (replaces OH with Cl or Br) |
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Term
| what are three ways of polymerization? |
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Definition
- radicals (using BzO)
- acid-catalysis (supplies an H+, creates a carbocation, stronger with electron donating groups)
- base-catalysis (occurs through carbocanion; stronger with electron-withdrawing group) |
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Term
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Definition
EDG: electron-donating group - this is a group that donates electrons to stabilize a carbocation in acid-catalyzed polymerization
EWG: electron-withdrawing group - a group that is electronegative and so stabilizes the extra electrons on a carbocanion in base-catalyzed polymerization |
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Term
| same side polymerization; alternating side polymerization; random side polymerization |
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Definition
| isotactic; syndiotactic; atactic |
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Term
| what are the two substances needed to perform Zeigler-Natta catalysis? |
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Definition
1. titanium chloride (TiCl3)
2. diethylaluminum chloride (Aluminum in the middle, bound to Cl an two ethyl groups) |
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