Exam 4 Spring 2004

Exam 4 Spring 2004 - Spring 2004 Organic Chemistry 322bL...

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Unformatted text preview: Spring 2004 Organic Chemistry 322bL April 21, 2004 4th Hour Exam Initial of Last Name I: Name Total T.A.’s Name (38 pts) (15 pts) (16 pts) (12 pts) (10 pts) (10 pts) - 1. Write the products of the following reactions. (38 pts.) m. a. (Era ffi? © 1' 6M, -CH2-CH=CD2 “ d. I A H3 NH2 CH3 1 0”“? CHBO NaOH/KOH 1) NaN02 / HCI H / CH3 1) NaNOZ, HCI 2)CuCN 100°C weak base u ‘ 1) NaN02 , HCI O k. [:3 —————» E?) 'L NM) Ph-CHZNHZ, dilute HCI '- <:>=O LiBH3CN O—NH’CVL‘IPK O\/H r“ l , _ (fl/11L? OH 3Ph-NHNH2 CE, ” NH. W ‘ f‘ /’t' NIH/H9 // $3 2. WF arm-(.10?) 2 Do either (a) or (b). if you do both only (a) will be graded. (15 pts.) H3 (a) Given to|uene prepare -' Br Br 1&3 $+mew my ' \ trifl— BV; NM); Q (Ev p6, H03, 9 (b) Given benzene prepare Q/ OH “'00: we; ms mg no ____.__a | ‘ / t mso / E; ———- V (Eat my 0,6»,0 0., M» mm. (LN a“ ,W 4—— -——"' Q HI on J. b ' WW“ Given aniline, toluene, sulfuric acid, chlorosulfonic acid, acetyl chloride, acetic anhydride, and any inorganic reagents you need prepare the sulfanilamide below. (16 pts.) NH2 0 q o a Place numbers next to the nitrogens in the biologically important heterocycle histamine: the most basic (1), the next (2), the least basic (3). In what type of orbital is the lone pair of electrons of the least basic N. In no more that ten words explain why it is least basic. (12 pts.) L+‘ O CH20H CHZO 5. Ho 0 H H CHQOH HO HO _ . If you dissolve the disaccharide above in water, does its specific rotation of plane polarized light change or not? Use chemical reactions or structure of functional groups to accéount for your answer. is it a reducing sugar? Does it react withTollens reagent Ag (NH3)2 in water? If so write the products of this reaction. (10 pts.) “Lowcfik’l/Mekax > i NolC and“; Sufi», Tomaéybt H H —CEN ————> + CH3 H2804 X E N ‘CDY K Write a reasonable mechanism for the fenetren of‘product B. (10 pts.) 905, 0% e 0'1 M ——></)\\)\ (fiw M fig? W “F945? )L/k P \ we; MM 14w e WNW ...
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Exam 4 Spring 2004 - Spring 2004 Organic Chemistry 322bL...

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