Term
| Add Water to the Double Bond |
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Definition
1. Acid-catalyzed hydration (H2SO4) Trans, Mark
2. Hydroboration (BH3, then H2O2 and NaOH) Cis, Non-Mark
3. Oxymercuration (Hg(OAc)2, then NaBH4) Trans, Mark
KNOW THIS REACTION x3 |
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Term
| Form Ethylene Oxide (specific) |
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Definition
| Use Ag catalyst and ethylene in air |
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Term
| Halogenate (X2) the Triple Bond |
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Definition
Use 1 or 2 mol X2 and CH3COOH
If 1 mol, trans addition |
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Term
| Convert an Alcohol to a Haloalkane |
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Definition
Use HX in water. If alcohol is 3o or 1o with beta branching, the intermediate is a carbocation. If the alcohol is 1o with no beta branching, the reaction proceeds with Sn2.
KNOW THIS REACTION x3 |
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Term
| Add X2 to the Double Bond |
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Definition
Use X2 in CH2Cl2, trans addition.
KNOW THIS REACTION |
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Term
| Add XOH to the Double Bond |
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Definition
Use X2 in water. Trans, Mark
KNOW THIS REACTION |
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Term
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Definition
1. Acid-catalyzed ring opening (H2SO4 and the nucleophile, OH attacks such that most stable carbocation is formed)
2. Nucleophilic ring opening (nucleophile and its salt, attack occurs at least sterically hindered carbon)
KNOW (2) |
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Term
| Brominate at the Allylic Position |
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Definition
| Use NBS, light, CH2Cl2. Radical mechanism. |
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Term
| Hydrate an Alkyne to a Ketone or Aldehyde |
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Definition
1. Hydroboration (Same reagents as alkene reaction) forms both ketone and aldehyde based on triple bond position
2. Acid-catalyzed hydration (H2SO4 and HgSO4) forms only ketones |
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Term
| Form an Alkyne from an Alkene |
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Definition
| Double dehydrogenation (X2 and CH2Cl2 THEN NH4(l)) |
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Term
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Definition
X2, light by radical mechanism
KNOW THIS REACTION |
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Term
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Definition
| Use OsO4 on the double bond. Cis addition of OH forms glycol (diol). |
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Term
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Definition
| Use O3, forms carbonyl groups at both ends. |
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Term
| Form a Ketone or Carboxylic Acid from an Alcohol |
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Definition
1. Use H2CrO4, forms Carboxylic acid if starting from 1o, forms Ketones if starting from 2o alcohol
2. Use PCC, forms Ketone if starting from 1o alcohol (stops short) |
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Term
| Add H2 to the Triple Bond |
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Definition
1. H2 and Pt, Proceeds to completion (yields alkane)
2. H2 and Lindlar catalyst (Usually palladium), forms cis alkene |
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Term
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Definition
1. First X2 and H2O, then NaOH and H2O (nucleophilic substitution conserves alkene stereochemistry)
2. Peracetic acid, CH2Cl2 (also conserves alkene stereochemistry) |
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Term
| Convert an Alcohol to an Alkoxide |
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Definition
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Term
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Definition
1. Williamson Ether Synthesis (R-OX and alkoxide ion)
2. Acid-catalyzed dehydration synthesis (H2SO4 at 140oC)
3. Acid-catalyzed addition of alcohol to alkene (H2SO4, with 1o alcohol) |
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Term
| Add H2 to the Double Bond |
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Definition
1. Use H2 and Pt, Cis addition
2. Use H2 and (S)-BINAP RuCl3, Trans addition |
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Term
| Form a Bromoalkane from Alcohol |
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Definition
Use PBr3
KNOW THIS REACTION |
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Term
| Form a Chloroalkane from Alcohol |
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Definition
Use SOCl2 and Pyridine or Et3N
KNOW THIS REACTION |
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Term
| Add HX to the Double Bond |
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Definition
Use HX, trans addition
KNOW THIS REACTION |
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Term
| Form an Aldehyde from Alcohol |
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Definition
| Use PCC; the alcohol must be 1o |
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Term
| Add HX to the Triple Bond |
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Definition
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Term
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Definition
Acid-catalyzed dehydration (H2SO4)
KNOW THIS REACTION |
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