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KwonChem30CExam1Key - Chem 30C Winter 2008 1St Midterm Exam...

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Unformatted text preview: Chem 30C, Winter 2008 1St Midterm Exam Prof. Ohyun Kwon, UCLA Agww Me ([2 Your Name (Please Print) Question Your points 1 (15 points) ‘ 5 2 (18 pe1nts) l (5 31(16 pe1nts) [ 1:: 4 (12 pomts) \ Z 5 (18 points) I (5 6 (21 points) Ll Total (100 points) Chem 30C 1“ Midterm, Page 1 l. (15 points) Show how to synthesize the following products from the given starting materials. (b) Chem 30C 1“ Midterm, Page 2 2. (a) (6 points) Draw structural formulas for these compounds. 2? Pyridine 3,4—Dimethoxyaniline Lithium diiospropylamide (LDA) & . £0” 0 W W? X‘s/L Rx NH: L‘- W L;" (b) (6 points) What are the common names of the molecules below? 0 \N N/ ”6 002m A '/> 0‘“ ~\ YO o N N / I thiiefinQ nrwfine comma (c) (6 points) Name the following molecules and the ion pair. OHCx/OH 1 .3'A'Ik1A‘VUKVYYUYQnK‘ Lal‘t‘c’r 0‘1th L”) N O 20' Emirmecirmmhm (Liniofiép m»: two“”Mia—Wand (T P” We“) Chem 30C lSl Midterm, Page 3 3. (l6lpoints) Provide starting material(s) or product for each transformation. .--. c "3 2,"- Jr W5 y! Lira. if? (a) M 1. NaOEt, EtOH 1. NaOH, H20 EtO CE 2. HCI, H20 @018- 2. HCI. H20 3. heat ammo2 NaOH NaNo2 0” H Ni, H2 HCI 1‘ N07- (b) 1. NaOH ‘ Ph + P}, - .-.. 2. H30, heat 0 (c) O 1. NaOH, H20 / H O 2. HCI, H20; and then heat C10H14O Chem 30C 1"l Midterm, Page 4 4. (12 points) Provide structural formulas for the products of each reaction step. 5‘} 117%"? (a) ' NHz . - 2 equ Mel Us ' Ph 0 1. NaOH, H20 2. HCI, H20 3. heat 1 CHO ' (:E ,NaOH CH0 2 H30, heat 0 O > 1 equiv LDA, -78 °C Br Chem 30C 1“l Midterm, Page 5 5. (18 points) Show how to facilitate the following conversions. Chem 30C 1‘“ Midterm, Page 6 6. (21 points) List the following compounds in order of decreasing acidity. 9 '2 EL” 0 + Ki” 0””20 [59‘ NH4 u H'N‘H N H2N NH2 ii 3 Most acidic r/Ct Q 5.1L ‘ H J, Q“ * {mu “LIL t g C}? u 1, ’ H + Least acidic ' 1:11 H ...
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