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Assignment 9 Answers - CHM 2120 Assignment 9 ANSWERS In...

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CHM 2120 – Assignment 9 ANSWERS In this assignment: - Esterification - Saponification of esters - Chemistry of carbonyl derivatives - Synthesis of carbonyl compounds (via oxidation of alcohols, etc) For the brainstorming/analysis portions of a synthesis, you must show where the required starting material is located in the product, identify all bond that are broken and formed (including H’s), and suggest a few reaction that might be appropriate (naming them is sufficient). 1. Give the IUPAC names or accepted trivial names for the following molecules: a) 1,1-diphenylbutan-1-ol b) butyl butanoate c) 4-methylpentanoyl chloride d) N,N -dimethyl-3-methylbenzamide e) 3-methylbenzoyl chloride f) methyl 4-hydroxy-3-methoxybenzoate g) 3-methylbutyl (E)-but-2-enoate h) sodium butanoate i) phenyl acetate; phenyl ethanoate j) 2-amino-5-phenylpentanoic acid k) butanamide l) N,N -dimethyl-3-hydroxybutanamide m) 5-bromo-4-chloropentanoic acid n) isopropyl pentanoate or 1-methylethyl pentanoate 2. Draw structures for a. 2-methylbutyl pentanoate b. N -benzyl-2-bromobutanamide c. 3-nitrobenzoyl chloride d. p -nitrophenyl acetate e. meta -dinitrobenzene f. 2-chlorobutanoyl chloride g. Triphenylphosphine h. Triphenylphosphine oxide i. Diazomethane (the two most important resonance structures) O O N H O Ph Br Cl O NO 2 O 2 N O O N O O NO 2 a) b) c) d) e) Cl O P P O H 2 C N N f) g) h) i) H 2 C N N Cl
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Assignment 9 ANSWERS 2 3. The aldol reaction can be accomplished using an acid catalyst. Give a mechanism for the following transformation: Ph O Ph H O H + Ph O H H B Ph CH 2 O H Ph H O H Ph H O H enol = weak nucleophile protonated aldehyde= activated electrophile Ph H C O H Ph OH H B Ph C H O H Ph OH H Ph C H OH Ph OH H Ph C H O Ph H B Ph C H O Ph B = conjugate base of acid or solvent
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Assignment 9 ANSWERS 3 4. Propose a synthesis of the following compounds. A “brainstorming” and retrosynthetic analysis must also be included. a. O Ph OH from O and any other required reagents Identify the cyclohexanone ring present in starting material (S.M.) and product (P), then identify the new bond. - The 1,3 relationship between the oxygens suggests that an aldol reaction would be appropriate 1 2 3 O Ph OH O H Ph O O Note that the ketone contains only 1 type of alpha proton and that the aldehyde does not possess α -protons. It is therefore not necessary to make the enolate separately (although still acceptable). Synthesis: S.M. + benzaldehyde O Ph OH NaH b. O OH from and any other required reagents 2-hexanone O O H O O Synthesis: O LDA O kinetic enolate H O Li O O NH 4 Cl (weak acid) Product 1 2 3 *A 1,3-relationship suggests that an aldol reaction would be appropriate. The required starting material, in blue, has been mapped on to the product (this could also be done by circling or numbering the atoms in starting material and product)
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Assignment 9 ANSWERS 4 c. (Question 4 continued) O Ph from O and any other required reagents - Double bond made from e l i m i n a t i o n reaction, Wittig O Ph OH 1 2 3 - 1,3 relationship allows for an aldol reaction--an excellent way to make new C-C bonds O Ph vs LG how to make the new C-C bond?
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