30cm1 - Name (Last, First, MI): Student ID Number: My TA is...

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Unformatted text preview: Name (Last, First, MI): Student ID Number: My TA is (circle one): Phil Haussmann or Luis Campos Chem 30C Fall 2005 Midterm # 1 Friday, October 28 Points Awarded Problem # Possible Points 1 21 1 8 1 1 16 12 10 100 ***Do not open this exam until instructed to do so*** ***Write all answers in the boxes or spaces provided*** —7 Pages Follow- Problem 1. Draw the major product in the box provided. For a multi—step synthesis, give the final product only (i.e. do not draw intermediates). ( 3 points each) a. H WN 1. HCI, CuCI, heat —-—-——-———> M C ; H20r04 d. /\/n\ 1, HCECMgBr ————> H O ' Ph \ CH3 N; o \ H 2. H30+ Problem I is continued on page 2 6 .Cl NH ' o 1. NaN02, HBr —————————————-———-—> 2. CuBr f 2 1. NaOEt, EtOH ————> CE 2. HCI, H20 1. g. {O N Cl ————--—-——> 6 2- BED Problem 2. Draw the intermediate, product, or reagent in the box provided. (3 points each box) a. COOEt 1. CH3COOEt, NaOEt —"‘"""""—'> 2. HCI, H20 COOEt NaOH, H20 EEO - O b' - 0 Ph/\/“\ Ph ————-—-——> “2” 0/ H Ph Ph Problem 3. Provide a reasonable synthesis of benzyl bromide from the following starting material. (11 points) NH2 CH3 CHzBr NH2 Problem 4. The following product was synthesized using an acid-catalyzed aldol reaction. In the box provided, draw the starting material(s) only (i.e. no intermediates) that would yield the given product. (8 points) Problem 5. Classify the following molecules as aromatic, antiaromatic or nonaromatic. Assume all molecules are planar. For each molecule state the number of p orbital electrons. Write your answers on the lines provided. (16 points) . 69 indole classification: —-——— classification: pi electrons: —— pi electrons: \ N / \ B—H k i / \N s classification: —— classification: pi electrons: ————— pi electrons: Problem 6. Draw the following compounds and rank them in order of increasing acidity: o-fluorophenol, styrene, o-nitrophenol, and cyclohexanol. Briefly explain your ranking. (12 points) Problem 7. Give the IPUAC names of the following compounds on the lines provided. (2 points each ) NH2 NH2 H30”, Problem 8. Propose a reason why aryl diazonium salts are more stable than alkyl diazonium salts. (10 points) ...
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This note was uploaded on 05/02/2008 for the course CHEM 30C taught by Professor Kwon during the Spring '08 term at UCLA.

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30cm1 - Name (Last, First, MI): Student ID Number: My TA is...

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