W08 midterm1 key

W08 midterm1 key - Organic Chemistry 30B Winter 2008 EXAM...

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Unformatted text preview: Organic Chemistry 30B Winter 2008 EXAM l, Page 1 Name I. SPECTROSCOPY l. a) (12 points) Give the number of expected signals (ignore splittings) in the 1H and 13C NMR spectra of the following compounds: [H NMR: 2’ . ’l 13CNMR: A b) (18 points) Sketch the 1H NMR spectrum for the compound below. Be sure to consider chemical shifts, coupling patterns, and relative intensities between each type of proton when drawing your spectrum. Label all non-symmetrically related H’s on the structure (e.g. a,b,c, etc) and show with an arrow which peak they correspond to on the spectrum: H H ojfl [or W“ ’ (“Dull W94) 10 9 8 7 6 5 4 3 2 1 0 (ppm) 7’ Organic Chemistry 30B Winter 2008 EXAM 1, Page 2 ?/ Name 2. (15 points) A compound with molecular formula C6H14 has the following 13C NMR spectrum. Assign the signals on the spectrum and provide its structure in the box below: 0 Degree of Unsaturation: xZ)+ Z ~/§/ Z I) 2—0 2M- pound C5H14 (Assign peaks on or elow the spectrum) Organic Chemistry 30B Winter 2008 EXAM 1, Page 3 W Name 3. (15 points) A compound with molecular formula CEHMO4 has the following IR spectrum. Its 13C NMR spectrum has only two lines. From this information only, deduce its structure and assign any recognizable peak. Provide 2 peak assignments to get maximum credit: Degree of Unsaturation: (g x;)+ 2 — /‘f Dill-1’“: 0 ’Z Compound C5H14O4 l i M: IR spectrum: TR HNSHITTHHC El kl so: 1% S “00 3000 2001] 15m 1000 5110 HHVEHUHB ERI ~I| 5’7 Cit .44 LL 5 4 C- g vhalf Dlt‘ Organic Chemistry 3013 Winter 2008 K EXAM l, Page 4 , Name 4. (40 points) A compound has the molecular formula C12H1402. Deduce its Structure from the IR, 1H NMR, and 13C NMR spectra given below. You MUST provide all the relevant information (peak assignments) to get maximum credit. Draw the structure in the box provided: 6 Degree of Unsaturation: ('(zxzflz v/L/ k :é 2/ compound C12H1402 IR (KBr; assign all recognizable IR stretch frequencies): 100 3 '2 Y Lu ' § L \ (sololeLZjOCZ a 9F V” II {79’ C r H \ O , 7‘!" 3 3 C' H sh . 05.00 m0 200. I 1300 1000 "0 m ‘ ' '43 Zr C=© Organic Chemistry 30B Winter 2008 EXAM 1, Page5 W k Name r 1H NMR: Draw the structure here as well and label all non—symmetrically related H’s on the structure (e.g. with a,b,c, etc). Show which peak the labels correspond to on the spectrum by drawing arrows to them. Provide labels for integration values (1H, 2H, 3H) and peak multiplicities (splitting type): ICD l 3% A... 2: N Q ‘"‘"‘§~ e M m :@ DIE® Mr 1:0 Organic Chemistry 30B Winter 2008 W [ EXAM 1, Page 6 ‘? Name 13C NMR spectrum for question 4. Draw the structure here again and assign all of its 13C signals by drawing arrows to positions on the structure. For peaks in similar environment (e.g. 129 and 130 ppm), you can choose either one of two related positions on the structure: _ H _ O 5b O J: - Q r O o v <2- 3; —h o o “3 LO 0 _o co co L‘ L 8 1 L8 '— ‘ ‘1 F , E i E a“ _ 8 .— ’:\ E '— \J n— o \r O i “r E Q g ,_ .. ‘F 8 8 V'- ! r. i x L O o 5 l o V i ’ O “8 l— a Q 8 l 0- LD ‘ _ w 04) F Q ~— [ O o N ‘ v . —MW— ~ L N N N ...
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This note was uploaded on 04/05/2008 for the course CHEM 30B taught by Professor Rubin during the Winter '05 term at UCLA.

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W08 midterm1 key - Organic Chemistry 30B Winter 2008 EXAM...

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