UCLA CHEM 30B - practice midterm 2 key (9 pages)

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practice midterm 2 key



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practice midterm 2 key

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Pages:
9
School:
University of California, Los Angeles
Course:
Chem 30b - Organic Chemistry II: Reactivity, Synthesis, and Spectroscopy
Organic Chemistry II: Reactivity, Synthesis, and Spectroscopy Documents

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ORGANIC CHEMISTRY 30B Winter 2012 MIDTERM EXAM II On my honor I have neither given nor received any aid on this examination KEY NAME LAST FIRST use ink please MIDDLE SIGNATURE use ink please UCLA id TA circle name Problem 1 18 2 12 3 5 4 5 5 10 6 20 7 10 8 10 9 10 TOTAL Melissa Timothy Points 100 INSTRUCTIONS This a closed book exam Only exams written in ink will be considered for regrading page 1 10 Byron PART 1 NOMENCLATURE PHYSICAL PROPERTIES AND GENERAL CONCEPTS 1 18 points Please draw the line wedge dashed line structures that correspond to the following names O O OCH3 OH S 4 methoxyhexan 2 one 2 methylpropanoic acid O O H cyclopentyl cyclohexyl ether E pent 3 enal O O S Cl O O trans 1 4 dimethoxycyclohexane page 2 10 Tosyl chloride 2 12 points Considering the hydrogen atoms shown in boldface please rank the structures in each of the following sets in order of increasing acidity from 1 to 3 3 being the most acidic Please indicate your rankings within each box O N H 2 Ranking O S H 3 1 H H O O H H Ranking 3 1 2 O O H Ranking 1 Cl O O H O H 3 2 s 3 5 points As above please rank the structures in the following set 1 to 4 in order of increasing basicity 3 2 1 page 3 10 4 4 5 points Carboxylic acids have a high tendency to form self complementary hydrogen bonded dimers Within the box please draw the structure of the dimer formed by cyclopentyl carboxylic acid O O H O H O 5 10 points The following four 13C NMR spectra correspond to the following four isomeric compounds C6H10O in no particular order Please draw the correct structure of the corresponding compound within the box provided Only the structure within the box provided will be considered for credit 5 6 epoxi 1 hexene 1 2 epoxycyclohexene di 2 propenyl ether trans 2 hexenal page 4 10 page 5 10 PART 2 REACTIONS AND REAGENTS In this section please draw inside the corresponding box the correct structure of the reactans reagents or products expected for each of the following reactions For full credit please make



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