MT2 key - MT1 ’47 1 Please fill in the reagents or...

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Unformatted text preview: MT1 ’47? 1. Please fill in the reagents or sequence of reagents needed to perform the synthesis below. (8 points) Br N02 2. One ring of phenyl benzoate undergoes electrophilic aromatic substitution much more rapidly than the other. Which one? Why? (8 points) Points awarded Organic Chemistry II — X36.B Berkeley Extension EDP#416750 Name March 23, 2011 3. Please show a step-by-step mechanism that explains the formation of the product shown. Be sure to include intermediates, formal charges and relevant resonance contributors. (10 points) Page 3 of 12 Points awarded 4. Two possible products are formed form the following reaction. What are the products? Provide step-by-step mechanisms that account for both products. (10 points) Br? Two Products pfir ‘4‘ ./ “,q \(‘ Q Q ~> 15‘ b 5. What is the IUPAC name of the following compound? (4 points) '2 CH3 8 \ M r Ll —E«om~7;?"~°'°'f°”- Points awarded. Organic Chemistry II - X36.B Berkeley Extension EDP#416750 Name March 23, 2011 6. Which orbitals contain the lone pairs on the nitrogen atoms labeled iand ii in the imidazole ring? (4 points) “if {073 . --‘=‘ N H "b H ‘c II“ U) ‘0 m :"o N 00"“) ~\\ N \. - :-‘c “58 7. Which of the following cannot be prepared from benzene in two synthetic steps? (4 points) N02 Br r R ML no , wt (WK N02 Br p Br I 1 2 3 (D { Law-ark 8. What is the major organic product obtained from the following reaction? (4 points) 0 o 1. NaOCH2CH3 CHaCHzOH —-—-—--——-—> CH3CH20 OCHQCH3 2_ 0 Vb 3. H3O“ EtOzC COzEt EtOzC COzEt EtO 2C CO zEt EtO ZC CO zEt O H O (Q 2 3 4 O Page 5 of 12 Points awarded 9. What is the major organic product obtained from the following reaction? (4 points) 0 o o 0 HO 1. CH3Li WM 2. H30" 1 2 3 @ 10. What is the major organic product obtained from the following sequence of reactions? (4 points) 0 Cl 0 O :7 OCHZCH3 O N 1, O H A O O O (9 4 H O 2. H30+ Points awarded Organic Chemistry II - X36.B Berkeley Extension EDP#416750 Name March 23, 2011 11. What is the major organic product obtained from the following sequence of reactions? (4 points) 1. NaOH, H20 0 o 1. NaOCHZCH3 2A H30+ WES" “‘_"’ OCHon3 2 [\L/ \A 3. H3O* Page 7 of 12 Points awarded 12. Draw a rational mechanism for the Dieckman condensation of diethyl 3,5- dimethylheptanedioate to form ethyl 2,4-dimethyl—6-oxo-cyclohexanecarboxylate. (10 points) Use curved arrows appropriately. Show all relevant intermediate(s) and lone pairs of electrons and formal charges where appropriate. 0 O (l O o 1) NaOEt, EtOH OB w, 2) H20, HCI EtO A OEt U- " L C?) v o l \ E"' 0; \ (3‘ as g b O ‘ l " 9 l '1 )sm/>/.\o6* * aw Kj ’ 9 Points awarded Organic Chemistry II - X36.B Berkeley Extension EDP#416750 Name March 23, 2011 13. Compound C anc be prepared by two different synthetic routes as indicated below. Indicate the identity (structure) of compound C and the other indicated intermediates. Molecular formulae and key reagents are supplied in the synthetic paths. (15 points) v Acetone 4-methoxybenzaldehyde ———> H2 -OH 9 Pd/C 0 Compound A [CHHQOZ] ‘l O ' o / °\ Compound B [CHHMOZ] 1. excess l2 / OH“ 2. H30+ m o O \ Compound C [C10H1203] ‘ Chromic Acid COmpOUHd E [C10H1402] _ AICIS _ Anisole(Methoxybenzene) _—+ 2. H202/ OH 0‘ Compound D [C10H1ZO] Page 9 0f 12 Points awarded 14. Which is the stronger acid, 4-methoxybezoic acid or 4-nitrobenzoic acid? Explain your reasoning. (5 points) t) Lo' 1/ s. a l +7 y} 5’ \‘Q. C) A . \Lor + r r ' + H .r q] __ O \ p (3, Mme 710»? 15. Rheosmin, a raspberry flavoring agent known since the 1920’s, can be prepared in two steps from 4—hydroxybezaldehyde and acetone in two steps. Please provide the reagents needed to affect this transformation. Also provide structures of intermediate products. (10 points) 0 HO Rheosmin "Rasberry Ketone" Points awarded Organic Chemistry II - X36.B Berkeley Extension EDP#416750 Name March 23, 2011 16. Consider the aldol condensation shown below. Deprotonation of the 3-methylbutan-2-one affords the opportunity for two different enolate anions to form, each of which results in one of the products shown, after condensation with propanal. 12 points. The product observed will depend upon whether the reaction was under knietic or thermodyanmic control, resulting from specific reaction conditions used. 1) LDA, o 00 Draw the structure of the associated intermediate enolate anion Results when an excess of ketone or Lg was used? Thermodynamic or Kinetic product? Page 11 of 12 Points awarded 17. Draw the forward reaction sequence that would be necessary to prepare the target compounds listed below. In addition to the starting material shown, you may use any inorganic reagents desired. You may also use any other reagents with five carbons or fewer and any number of non-carbon atoms. (Remember the retrosynthesis is shown below. The product is on the left and reactants are on the right. You need to draw the forward reaction sequence. Draw only the forward reaction sequence — not the mechanisms!) Provide the most efficient and shortest route to the target molecules. Show all reagents necessary. These syntheses will require several steps. You may combine steps (i.e. use 1, 2, etc. over the arrow) in ways similar to how we have done it in class. (12 points each) 0 O O 0 :3 W § 1.\ 4430* Q s l> LDR/flcam in» w q A MI‘JMJ 0 it Points awarded ...
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MT2 key - MT1 ’47 1 Please fill in the reagents or...

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