Organic Chemistry 2 Test 1 – Flashcards
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| What is the pKa of HCl? |
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| -8 |
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| What is the pKa of H3O+? |
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| -2 |
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| What is the pKa of NH4+? |
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| +9 |
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| What is the pKa of NH3? |
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| +35 |
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| What is the pKa of H2O? |
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| +16 |
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What is the pKa of -*ROH?
*Note: "R" is a generic representation for various alkyl groups. The bulk of the alkyl group can impact acidity, but for a ballpark pKa value, this works. |
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| +16 |
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| What is the pKa of -RCOOH? |
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| +5 |
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| What is the pKa of phenol? |
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| +10 |
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| What is the pKa of p-toluene sulfonic acid? |
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| -3 |
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| What is the pKa of -RCOCH2COR-? |
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| +10 |
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| What is the pKa of -RCOCH3? |
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| +20 |
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| What is the pKa of HCCH? |
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| +25 |
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| What is the pKa of H2CCH2? |
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| +44 |
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| What is the pKa of CH4? |
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| +50 |
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| If you have nitrobenzene, which reaction would you use to make aniline? |
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Use Zn(Hg) and HCl or Fe and HCl or Ni and H2 or Sn and HCl |
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| If you have aniline, which reaction would you use to make nitrobenzene? |
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| CF3COOH |
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| If you have a COR- group on a benzene ring, how do you make that group into CH2R-? |
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Zn(Hg) and HCl or NH2NH2 and OH- |
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| If you have a CH2R group on a benzene ring, how do you make that group into COR-? |
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| CrO3, H2SO4, H2O and heat |
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| If you have SO3H on a benzene ring, how do you get benzene? |
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| H2O, cat. H2SO4 and heat |
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| If you have aniline, how do you make the NH2 group into HNCOCH3? |
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| H3CCOCl and pyridine |
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| How do you remove the -COCH3 group from -NH on a benzene ring to get aniline? |
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| NaOH and H2O |
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| How do you make a OCOCH3 group on a benzene ring starting from phenol? |
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| H3CCOCl and pyridine |
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| How do you remove a H3CCOO group from a benzene ring to get phenol? |
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| NaOH and H2O |
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| How do you get anisole from phenol? |
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| NaOH and CH3I |
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| How do you get phenol from anisole? |
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| With concentrated HI |
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| How do you prepare an acid chloride (-RCOCl) from a carboxylic acid (-RCOOH)? |
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| With SOCl2 |
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| Describe the halogens (I, Br, Cl, F) in terms of activating/deactivating, EWG/EDG, and directing effects. |
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| The halogens are weak deactivators, weak EWGs, and o and p directors. |
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| Describe carbonyl groups (-C=OR) in terms of activating/deactivating, EWG/EDG, and directing effects. |
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| The carbonyl groups are moderate deactivators, moderate EWGs, and meta directors. |
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| Describe -CN, -SO3H, -NH3, -NH2R, -NHR2, -NR3, -CF3, -OH2, and -NO2 in terms of activating/deactivating, EWG/EDG, and directing effects. |
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| These are all strong deactivators, strong EWGs, and meta directors. |
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| Describe -NH2, -NHR, -NR2, -OH, and -OR in terms of activating/deactivating, EWG/EDG, and directing effects. |
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| These are all strong activators, strong EDGs, and o and p directors. |
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| Describe alkyl, phenyl, and vinyl groups in terms of activating/deactivating, EWG/EDG, and directing effects. |
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| These are all weak activators, weak EDGs, and o and p directors. |
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| Describe -NHCOR and -OCOR in terms of activating/deactivating, EWG/EDG, and directing effects. |
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| These are moderate activators, moderate EDGs, and o and p directors. |
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| What is the Lindlar catalyst and what does it do? |
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Pd-CaCO3, Pb(OAc)2, and quinoline
It hydrogenates alkynes to cis alkenes. |
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| How do you hydrogenate an alkyne to a trans alkene? |
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| Use sodium metal (Na0) and liquid ammonia (NH3(l)). |
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| What are the reagents involved in mercury ion catalyzed hydration of an alkyne? |
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| H2SO4, H2O, and HgSO4 |
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| In mercury ion catalyzed hydration of alkynes, does the H2O add to the alkyne according to Markovnikov's rule? |
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| Yes. The O adds to the most highly substituted C. |
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| Which reagents are used in anti-Markovnikov hydration of alkynes? |
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1) BHR2 2) H2O2 and OH- |
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| What do we use NBS for? |
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| Adding a single Br to an alkene, as opposed to creating a viinal dihalide, as occurs with excess Br. NBS keeps the concentration of Br very low. Br will add wherever a radical can form (on allyic Hs). |
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| Do organolithium reagents (R-Li) add 1,2, 1,4, or both to enones? |
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| 1,2 |
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| Does LiAlH4 add 1,2, 1,4, or both to enones? |
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| 1,2 |
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| Does NaBH4 add 1,2, 1,4, or both to enones? |
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| 1,2 |
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| Do grignard reagents (RMgX) add 1,2, 1,4, or both to enones? |
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| both 1,2 and 1,4 |
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| Name 3 methods for forming an enone. |
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1) Aldol condensation 2) Mono alpha-halogenate (acidic conditions), followed up by basic E2 H-X elimination 3) Oxidation of an allylic alcohol using MnO2 |
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| Do organo cuprates (R2CuLi) add 1,2, 1,4, or both to enones? |
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| 1,4 |
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| Does RMgBr + copper salts add 1,2, 1,4, or both to enones? |
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| 1,4 |
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| Do enolates add 1,2, 1,4, or both to enones? |
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| 1,4 (net) |
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| Does hydroxide (OH-) add 1,2, 1,4, or both to enones? |
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| 1,4 (net) |
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| Do alkoxides (OR-) add 1,2, 1,4, or both to enones? |
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| 1,4 (net) |
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| Do amines add 1,2, 1,4, or both to enones? |
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| 1,4 (net) |
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| What do you get when you add H3PO2 to an arenediazonium ion? |
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| Benzene |
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| What do you get when you add H2O to an arenediazonium ion? |
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| Phenol |
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| What do you get when you add CuBr to an arenediazonium ion? |
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| Bromobenzene |
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| What do you get when you add CuCl to an arenediazonium ion? |
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| Chlorobenzene |
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| What do you get when you add CuCN to an arenediazonium ion? |
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| A nitrile group on a benzene ring (C triple bond N substituent) |
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| What do you get when you add HBF4 to an arenediazonium ion? |
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| Fluorobenzene |
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| What do you get when you add KI to an arenediazonium ion? |
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| Iodobenzene |
