Acidity of Carbonyl Compounds
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1 Acidity of Carbonyl Compounds 1. All of the following compounds have acdic C bonds. The pka of each compound is indicated: Compound pka Conjugate Base 11 etc. 13 etc. C 2 20 C C More resonance: more stable conj.base C 2 25 C C Ester is electron donating, which is less stable conj. base. N C C 2 31 N C C N C C With each of the above compounds: identify the most acidic proton of each compound draw each conjugate base use resonance structures to show stabilization of the conjugate base rationalize the acidity order shown predict and explain the order of nucleophilicity of the conjugate bases Nitrogen is less electronegative. The conjugate bases at the bottom (high pka) will be the most nucleophilic. 2. Provide reasonable curved-arrow mechanisms for keto-enol tautomerization in acid and in base: : 2 3 : 3. The following molecules are both ketones, and are structurally similar. owever, they display strikingly different basicity. Explain this observation. pka = 40 pka = 20 can't form N enolate (edt's ule violation) base forms enolate base Chemistry E-2b Week 6 1
2 Basic Aldol and Claisen Mechanisms 1. Provide a mechanism which explains why only one is replaced with a D. D: Me NaD, D 2 Me D Me Me prefer to remove axial because of D D Me overlap with prefer to protonate C= * orbital in axial position to maintain chair and avoid Me in axial position Me : 2. Predict the product, and provide a curved-arrow mechanism for each of the following transformations. NaMe :Me Aldol Condensation Me :Me Me Me NaMe Me Me :Me Me Me Me :Me Me **Note: if you want to get the neutral product you need to do workup Claisen (or Dieckmann) Condensation Chemistry E-2b Week 6 2
3 More Aldol and Claisen Mechanisms 1. Provide curved-arrow mechanisms for the following transformations: Na : Why deprotonate at that carbon? Any other possibilities would give less stable 4-membered ring. 5- and 6-membered rings are nearly always preferred. : 3 Acid-catalyzed Aldol addition : 2 : 2 Chemistry E-2b Week 6 3
4 Enol and Enolate Mechanisms 1. Provide a curved-arrow mechanism for each of the following transformations. 2 trace :Solvent Ts Ts NaCN (hint: CN is also acting as a base) CN :CN Ts C N Ts C N :CN (this is a "nitrile enolate") Chemistry E-2b Week 6 4
5 Still More Aldol and Claisen Mechanisms 1. Provide curved-arrow mechanisms for the following transformations: Na : condensation reverse Aldol proton : transfer forward Aldol C 3 Mg (1 equiv) Na " :C 3 " condensation C 3 : proton C 3 transfer forward Aldol Chemistry E-2b Week 6 5
6 Synthesis using Aldol and Claisen eactions 1. Propose synthetic pathways for the following multistep transformations. An aldol or claisen reaction will form a crucial step in each synthesis. NaMe 1. LiAl 4 Cr 3 (dry) 2. workup Cl K t Bu or Na (must be a non-nucleophilic strong base) coumarin (first synthetic perfume) (It would be possible to do the esterification and aldol condensation in 1 step.) Chemistry E-2b Week 6 6
7 Decarboxylation: Mechanisms and Synthesis 1. Provide a curved-arrow mechanism for the following transformation. C 3 NaC 3 (excess) 1. Na 2. 3 :C 3 tautomerize C 2 C (show ester hydrolysis) C 3 C 3 C 3 :C 3 2. Using starting materials containing no more than 3 carbons, synthesize the following target using a route that involves as the final step. C 3 C 3 1. NaC 3 2. workup C 3 NaC 3 C 3 NaC 3 C Chemistry E-2b Week 6 7
8 Putting It Together: ecognizing Acyclic "Aldols" 1. Identify the starting materials which could produce each of the "skeleton" products below, give the name of the reaction, and provide the reagents necessary to carry out both steps of the transformation. NaEt 2 aldol addition aldol condens. Et Et 1. NaEt 2. wkup Et , Claisen condensation Et NaEt Et , enolate alkylation (acetoacetic ester synthesis) Et ' NaEt ' Et , ' enolate alkylation (acetoacetic ester synthesis) Chemistry E-2b Week 6 8
9 Putting It Together: ecognizing Cyclic "Aldols" 1. Identify the starting materials which could produce each of the "skeleton" products below, give the name of the reaction, and provide the reagents necessary to carry out both steps of the transformation. (The strange curved loops below are meant to represent a ring of any size; most common are 5- and 6-membered rings.) NaEt 2 aldol addition aldol condens. NaEt 2 aldol addition aldol condens. Et NaEt Et , enolate alkylation (acetoacetic ester synthesis) Et Et NaEt Et , Dieckmann synthesis (intramolecular Clasisen) Et NaEt Et , enolate alkylation (acetoacetic ester synthesis) Chemistry E-2b Week 6 9
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