CHEM 372 Lecture Notes - Lecture 20: Nucleophilic Conjugate Addition, Michael Reaction, Claisen Condensation

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cerisewhale850

11 Aug 2015

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Chapter 23, 3rd edition: 1, 5-20, 21-28, 30, 32-34, 45-54, 58, 59, 64, 65. Chapter 23, 4th edition: 1, 2, 4-6, 10-13, 16-20, 21-28, 32-36, 38, 39, 44-48, 50-53, 58, 62. Chapter 24, 3rd edition: 1-10, 12-16, 18-24, 25-26, 27-33, 35-39, 43, 44-45, 47, 48, 54, 62-62 (synthesis problems!) Chapter 24, 4th edition: 1-10, 12, 13, 15-18, 20-25, 28-30, 31, 32, 35, 37, 38-42, 43-47, 49, 54, 56, 62-64. Warm-up problems: draw the products for the following intramolecular aldol and claisen condensations. Recall conjugate addition reaction between a nucleophile and enone: An enolate can be a nucleophile in a conjugate addition reaction: the michael reaction: usually (but not always) requires: A very stable enolate, such as one from a diester or diketone. An enone (or equivalent: the enolate is called the michael donor, the enone is called the michael acceptor, overall reaction: a michael addition results in a 1,5-dicarbonyl compound:

Related Questions

Please answer all the questions!

Nitrobenzene + Br_2/Fe + heat yields which product(s): a. m-bromonitrobenzene b. o-bromonitrobenzene c. p-bromonitrobenzene d. both b & c acetophenone + Br_2/Fe + heat yields which product(s): a. m-bromoacetophenone b. o- bromoacetophenone c. p- bromoacetophcnone d. both b & c cumene + HNO-3/H_2SO_4 + heat rightarrow a. m-nitrocumene b. o-(2-CH(CH_3)_2)benzenesulfonic acid c. o & p-nitrocumene d. something else! Which is the most acidic? a. cumene b. 4-nitroaniline c. 4-nitrophenol d. 4-methoxyphenol e. 4-methylphenol Which is the most basic? a. cumene b. 4-nitroaniline c. 4-methoxyaniline d. 4-chlorophenol c. 4-methylphenol nitrobenzene + acetyl chloride - AICl_3 rightarrow a. o-CH_3(C = O)NO_2benzene b. p-CH_3(C = O)NO_2 benzene c. p-CH_3 -(C = O)NO_2 benzene d. a & b e. no rxn benzene + 1. Br_2/FeBr_2 followed by 2. H_2SO_4/SO_3 rightarrow a. o-bromobenzenesulfonic acid b. p-bromobenzenesulfonic acid c. both a & b d m isomer e. no rxn benzene + 1.. H_2SO_4/SO_3 followed by 2. Br_2/FeBr_3 a. o-bromobenzenesulfonic acid b. p-bromobenzenesulfonic acid c. both a & b d m isomer e. no rxn benzene + acetyl chloride + AlCl_3 followed by Cl_2/AlCI_3/heat rightarrow a. o-chloroacetophenone b. p-chloroacetophenone c. m-chloroacetophenone d. a & b e. no reaction! p-methylanisole + HNO-3/H_2SO_4/heal rightarrow a. 2-nitro-4-methylanisole b. 3-nitro-4-methylanisole c. 3-nitro-5-methylanisole d. no rxn e. something else toluene + KMnO_4/OH^-/heat, then dilute acid quench, followed by HNO_3/H_2SO_4 rightarrow a. 3-nitrotoluene b. 4-nitrobenzenoic acid c. 3-nitrobenzoic acid d 2-nitrotoluene e. something else! a. 3-ehloroacetophenone b. 3-chlorophenol c. 4-chlorophenol d. 4-Chlorophenyl-l-ethanol e. a-d incorrect toluence + NBS/light, followed by NBS /light (repeat reaction a total of 3 times), then HNO_3/H_2SO_4 rightarrow a. 3-NO_2(Ph)CBr_3 b. 4-NO_2(Ph)CBr_3 c. 4-nitrotoluene d. 4-nitro-1, 3, 5-tribromobenzene e. a-d incorrect aniline + NaNO_2/HCI/zero degrees, then CuCN rightarrow a. benzonitrile b 2-cyanoaniline c. 4-cyancaniline d. both b & c e. 3-chloroaniline aniline + NaNO_2/HCI/zero degrees, then Cul a. 4-iodoaniline b. 4-nitroiodobenzene c. iodobenzene d. both a & b. e. something else! Do the following text problems: 1, 2., 3, 4, 5, 6, 7, 10, 11, 13, 14, 15, 17, 18, 23, 26, 28, 29, 30, 31, 36, 38, 39, 40, 42, 43, 45, 46, 48, 49, 50, 51, 55, 56, 61, 62

Make a small table of the K_{\alpha } values from table 9.1 (included below), the K_{\alpha }(calc) value and the corrected value K_{\alpha }^{*} (calc) along with the \lambda_{K_{\alpha }} value from the experimental value and the value calculated from K_{\alpha }^{*} (calc) energy for the following elements: B, Na, Cl, Fe, and Ag. (note this is college upper level physical chemistry; I expect a full answer)

Give It Some Thought 6.16

Valence electron configurations of the elements.

Part A

The elements Ni, Pd, and Pt are all in the same group. By examining the electron configurations for these elements in the following figure, what can you conclude about the relative energies of the nd and (n+1)s orbitals for this group?

nd > (n+1)s

nd < (n+1)s

nd = (n+1)s

It is impossible to conclude.

CHEM 372 Lecture Notes - Lecture 20: Nucleophilic Conjugate Addition, Michael Reaction, Claisen Condensation

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