CH 23: Carbonyl Condensation Reactions Renee Y. Becker CHM 2211 Valencia Community College.
Chemistry 234 Chapter 23 Problem Set Carbonyl Condensation ...
Transcript of Chemistry 234 Chapter 23 Problem Set Carbonyl Condensation ...
![Page 1: Chemistry 234 Chapter 23 Problem Set Carbonyl Condensation ...](https://reader031.fdocuments.net/reader031/viewer/2022012501/617a90921986b46aba02703b/html5/thumbnails/1.jpg)
Page 1 of 6
Chemistry234Chapter23ProblemSet
CarbonylCondensationChemistry1) Drawtheproductformedfromeachofthealdolreactions/condensationsbelow.
2) Whatstartingmaterial(s)is/areneededtoprepareeachcompoundbelowviaanaldolreaction?
H
O2
OHH2O
H H
O O+
OHH2O
O 1. LDA, THF -78 °C2. Ph O
3. HO-, H2O
OH
O
O O
OHH2O
OHH2O
O 1. LDA, THF -78 °C2. O
3. H2O
O
O
O
![Page 2: Chemistry 234 Chapter 23 Problem Set Carbonyl Condensation ...](https://reader031.fdocuments.net/reader031/viewer/2022012501/617a90921986b46aba02703b/html5/thumbnails/2.jpg)
Chem.234–Chapter23ProblemSet
Page 2 of 6
3) PredictthemajororganicproductformedfromeachoftheClaisenCondensationReactions.
4) EachcompoundbelowundergoesaDieckmannCondensation(IntramolecularClaisen).Predictthemajorproductsforeach.
5) Drawthecompleteelectronpushingmechanismforthesecondreactioninquestion4.
Ph OEt
O2
1. NaOEt HOEt2. H+ workup
OCH3
O+
Ph OCH3
O1. NaOCH3 HOCH3
2. H+ workup
O
+EtO OEt
O 1. NaOEt HOEt2. H+ workup
O+
Ph OEt
O 1. NaOEt HOEt2. H+ workup
EtO
OOEt
O
1. NaOEt HOEt2. H+ workup
2products
O
OEt
O
OEt
O
O
1. NaOEt HOEt2. H+ workup
1. NaOEt HOEt2. H+ workup
![Page 3: Chemistry 234 Chapter 23 Problem Set Carbonyl Condensation ...](https://reader031.fdocuments.net/reader031/viewer/2022012501/617a90921986b46aba02703b/html5/thumbnails/3.jpg)
Chem.234–Chapter23ProblemSet
Page 3 of 6
6) WhatstartingmaterialsareneededtosynthesizeeachcompoundbelowbyaCrossedClaisenReaction?
ConjugateAddition7) PredicttheproductforeachMichaelreactionbelow.
8) DrawtheproductfromtheRobinsonAnnulationofeach.
OO
OEtO
O
H
O
Ph
O+
OEt
OO OHH2O
O OOOHH2O
+
O+
Ph
O
OEt
O OHH2O
OHH2O
OHH2O
O
O
O
+
OO
+
O O+ OH
H2O
![Page 4: Chemistry 234 Chapter 23 Problem Set Carbonyl Condensation ...](https://reader031.fdocuments.net/reader031/viewer/2022012501/617a90921986b46aba02703b/html5/thumbnails/4.jpg)
Chem.234–Chapter23ProblemSet
Page 4 of 6
9) IdentifywhatreagentsyouwouldusetopreparethecompoundbelowusingaRobinsonAnnulationreaction?
Part5:ApplicationtoSynthesis10) Fillinthemissingreagentsinthesyntheticsequencebelow.
11) Provideareasonablemechanismforthereactionbelow.Whatisthedrivingforceforthisreaction?
12) Proposeanefficientsynthesisforthefollowingtransformation.Hint:YouwillneedtousetheozonolysisreactionfromorganicI.
O
O
O O
OEt
OO
OEt
O
O O
CNHOOCH2
OEt
OO O
O
Br
O
O
OH
OHH2O
O
O
O?
![Page 5: Chemistry 234 Chapter 23 Problem Set Carbonyl Condensation ...](https://reader031.fdocuments.net/reader031/viewer/2022012501/617a90921986b46aba02703b/html5/thumbnails/5.jpg)
Chem.234–Chapter23ProblemSet
Page 5 of 6
13) Challenge:Thecompoundbelowcannotbepreparedbydirectalkylationofcyclohexanone.Explainwhynotandprovideanalternativeroutetocarryoutthetransformation.Hint:atsomestage,methylcupratemightbeuseful.
14) Drawanelectronpushingmechanismforthefollowingreaction.
15) Deviseasynthesisforthecompoundbelowstartingwithcycloheaxnone.
O O
OO
H3CO
O1. NaOCH3
2. H2OO
O
OCH3O
O O
O
![Page 6: Chemistry 234 Chapter 23 Problem Set Carbonyl Condensation ...](https://reader031.fdocuments.net/reader031/viewer/2022012501/617a90921986b46aba02703b/html5/thumbnails/6.jpg)
Chem.234–Chapter23ProblemSet
Page 6 of 6
16) Deviseasynthesisoftheketonebelowusingtheesterstartingmaterialprovided.YoursynthesismustinvolvetheuseofaClaisencondensation.
17) Deviseanefficientsynthesisforthefollowingtransformation.
18) ReactionCombo:Drawtheorganicproductsformedwhenbutanalistreatedwitheachreagent.a) HO-,H2C=O,H2Ob) 1.LDA,THF,-78oC;2.PhCHO;3.H2Oc) diethylmalonate,NaOEt,HOEtd) CH3-LithenH+e) NaBH4,CH3OHf) HOCH2CH2CH2OH,H+g) H3C-NH2,traceacidh) (CH3)2NH,traceacidi) H2CrO4j) Br2,AcOHk) Ph3P=CH-CH3l) 1.LDA,THF,-78oC;2.H3C-Im) HO-,H2O(rxnbetweentwomoleculesofaldehyde)
OEt
O O
EtO OEt
OOO
![Page 7: Chemistry 234 Chapter 23 Problem Set Carbonyl Condensation ...](https://reader031.fdocuments.net/reader031/viewer/2022012501/617a90921986b46aba02703b/html5/thumbnails/7.jpg)