Organic Chemistry Practice Exam Carboxylic Acid Derivatives Enolate Chemistry and Carbohydrates
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In this video, I work through 40 specific examples that typically appear on a second semester organic chemistry exam. The main ideas covered are reactions of carboxylic acid derivatives, the reactions of enolates, and introductory questions about carbohydrates. • Raw worksheet: • https://docs.google.com/document/d/1J... • Questions begin at 0:40 • 1) Ranking reactivity of carboxylic acid derivatives 0:40 • 2) Determine which reaction occurs more readily 4:38 • 3) Base hydrolysis of an isotopically labeled ester 6:01 • 4) Ranking reactivity of carboxylic acid derivatives 8:31 • 5) Determining if the carbohydrate is a ketose or aldose 11:16 • 6) Acid hydrolysis of an isotopically labeled ester 13:24 • 7) Alpha hydrogens 17:14 • 8) Explain the product formation (selective deprotonatation of an alpha hydrogen) 20:40 • 9) Determining if the carbohydrate is a hexose or pentose 23:23 • 10) Identify the most acidic proton 24:33 • 11) Determine the number of chiral centers and total number of stereoisomers in carbohydrates 27:20 • 12) Draw all the possible enolates 30:17 • Reactions (13-36): • 13) Alcohol reaction with an acyl chloride 32:29 • 14) Total reduction of a ketone and ester with lithium aluminum hydride (LAH) 34:16 • 15) Acid hydrolysis of a nitrile 36:22 • 16) Multi-step reaction (includes oxidation, Sn2, and nucleophilic acyl substitution) 39:46 • 17) Aldol reaction (no heat) 42:07 • 18) Aldol reaction with a ketone (no heat) 45:05 • 19) Acid catalyzed imine formation 48:14 • 20) Gilman addition to an alpha,beta unsaturated ketone 50:11 • 21) Acetate reaction with an acyl chloride 52:07 • 22) Grignard reaction with an acyl chloride 53:08 • 23) Selective reduction of a ketone with sodium borohydride 55:03 • 24) Amine reaction with an anhydride 56:27 • 25) Aldol reaction followed by dehydration 58:10 • 26) Aldol reaction (no heat) 1:01:01 • 27) Claisen condensation 1:02:49 • 28) Addition to acetoacetic ester 1:06:56 • 29) Ozonolysis followed by an aldol reaction 1:08:26 • 30) Robinson annulation 1:10:55 • 31) Gilman reagent with an acyl chloride 1:13:56 • 32) Selective reduction of an ester with DIBAL 1:15:06 • 33) Acid catalyzed ester reaction with amine (aminolysis) 1:16:06 • 34) Alcohol stereochemical transformation 1:17:23 • 35) Intramolecular aldol reaction (no heat) 1:19:56 • 36) Micheal addition 1:22:14 • Synthesis questions (37-40): • 37) Carboxylic acid to amide 1:25:42 • 38) Alkyne to ester 1:26:57 • 39) Acetoacetic ester to functionalized acetoacetic ester 1:31:45 • 40) Functionalized acetoacetic ester to cyclic alpha, beta unsaturated ketone 1:37:58 • Nucleophilic addition to carbonyls: • • Nucleophilic Addition to Aldehydes an... • Alkene stability: • • Alkene Stability, cis/trans, and E/Z ... • Ranking acid strength: • • How to Rank molecules by pKa (Acid St... • Overview of Sn2 reactions: • • Overview of SN2 Reactions
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