KAHR exam2 - 6. {15 pts} Solomons 20.16. Butter yellow is a...

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CHEM 337 SPRING 2006 EXAM 2 (ANSWERS) 1.____2._____3._____4._____5._____6._____7._____8._____9._____10._____11._____ TOTAL SCORE_________ Check to see that your points add up to the total score awarded. If you have a more substantial question/concern please place these in writing with the entire exam attached in the mailbox of TA James Stewart. NAME_________________________________________________________ 1. {6 pts} The conjugate acid of one of the following compounds is much more acidic than the others. Circle that compound. 2. {12 pts} In the Gabriel synthesis of primary amines write the correct intermediates in the boxes provided.
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3. {15 pts} Solomons 19.22. Show how you could employ enamines in the synthesis of the following compound. O NH H + N CH 3 (CH 2 ) 4 C(O)Cl N + C(CH 2 ) 4 CH 3 O Cl - H 2 O O C(CH 2 ) 4 CH 3 O 4. {8 pts} How would you convert anthranilic acid to biphenylene? Write reagents and conditions above the arrow NH 2 COOH H 2 SO 4 /NaNO 2 (0-5°C) anthranilic acid biphenylene
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5. {9 pts} Assign the peaks in the followoing spectrum as (a), (b), or (c).
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Unformatted text preview: 6. {15 pts} Solomons 20.16. Butter yellow is a dye once used to color margarine. It has since been shown to be carcinogenic, and its use in food is no longer permitted. Outline a synthesis of butter yellow from benzene and N,N-dimethylaniline. N N N(CH 3 ) 2 HNO 3 H 2 SO 4 NO 2 (1) Fe, HCl (2) OH-NH 2 H 2 SO 4 /NaNO 2 (0-5C) N 2 + butter yellow N(CH 3 ) 2 7. {8 pts} Solomons 21.25. Explain AND illustrate how it is possible for 2,2-dihydroxy-1,1-binaphthyl (below) to exist in enantiomeric forms. OH OH OH OH HO HO Naphthyl hydrogens and hydoxyl groups cannot lie in the same plane. Steric hindrance. 8. {12 pts} Show the mechanism of the two step transformation of an allylphenylether to o-allylphenol using curly arrows. OCH 2 CH=CH 2 200C OH CH 2 CH=CH 2 O O H O-9. {15 pts} Draw the three intermediate structures in the boxes in the synthesis of cyclobutanecarboxylic acid from diethyl malonate and 1,3-dibromopropane. NaOH...
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KAHR exam2 - 6. {15 pts} Solomons 20.16. Butter yellow is a...

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