CH310M-POW-10_KEY - CH 310/318M_POW-10 Williams Fall 2010...

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Unformatted text preview: CH 310/318M_POW-10 Williams Fall 2010 Due Date: NOON Mon, 11/08/10 Name (print): Signature: Do Homework in PEN! Please write the first three ietters of your last name in the boxes CH 310/318M_POW-10 Williams Fall 2010 Due Date: NOON Mon, 11/08/10 1. Synthesis. Provide a synthesis for the preparation of 1,3-cyclohexadiene from cyclohexane. Show all reagents and intermediates necessary to get from starting material to product. A retrosynthetic analysis may help you plan your synthesis, but only the forward synthesis is required as the answer here. (2 pt) s’s’gr \ PW Nam Ha . \ 7: \h 1 M379 £2 . 1xa—f0 / "~— , . \ CML‘ XI- CH 310/318M_POW-10 Williams Fall 2010 Due Date: NOON Mon, 11/08/10 2. Fill in the Box. Fill in the reagents or product boxes according to the information given to you below. If the product is racemic or meso, indicate so by writing in the appropriate boxes. (3pts) 1) 03! 2) M923 ‘ NBS -—’/—l—l—h“ l J \ VLLanbU CH 310/318M_POW-10 Williams Fall 2010 Due Date: NOON Mon, 11/08/10 4. Mechanism. Eventually, we will learn how bromohydrins can react to give epoxides when treated with base. Based on your knowledge of nucleophilic substitutions thus far, use the arrow pushing formalism to indicate electron flow in the reaction given below. Be sure to show all lone pairs and charges where relevant! Also fill in the blanks with the appropriate words to complete the statement regarding this reaction. (2pts) NabH _—'——>- Ethanol gt Stereochemistry is "Ll-"l l RN{J&&" , l 2““ A I "\. I, ‘ .Ll l this is a <3 *4: 7’" displacement. {:28 ‘ l I l ' J kL: , I .r- 33! \\ l V. i c “L ' . '- - - CH 310/318M_POW-10 Williams Fall 2010 Due Date: NOON Mon, 11/08/10 3. Mechanism. Use the arrow pushing formalism to indicate electron flow in the radical halogenation of toluene given below. Remember to show all lone pairs and charges where relevant, and include all steps in the radical mechanism! (3 points) CH CH B 3 NBS, 2 r —r~ och, lJlXLjVKLKlQLmi ‘_ H k, A/ i Ar. 542%" ’ll) 11, /\[l\‘j n %V: _ / /J H / ll\/ ° v , .‘5; i; <7, .. K» , 15 /:(C"lz , L L I‘m / /C1l1127 I, ,/ R—p i‘ iaV . lQ/bwrmub M ' “a. NO“ I) L I: Q h l/ H‘ q a” H "l c 1%(Y‘IL-AM c. Tiv L Mr,» Pyri- QJ Q :97»; "-7 0J4?” . 10' 5:5. 3) /> M l /#\(/Cll2/BV I LLyl/ fa h” Ea i/JTI‘“. 451 l: {l 7" \ 1‘ 4 7 ll T ...
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