215W16_E2_key_with+stats

215W16_E2_key_with+stats - Dear Chem 215 students The exam...

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Dear Chem 215 students, The exam statistics are provided below. This represents a great job on exam 2! Average: 89/120 (74%) Standard deviation: 23.5 Median 95/120 high: 120/120, low: 0/120 number of students: 813 The scores are now posted on CTools under gradebook. A pdf copy of your exam will be posted to your M-­‐Box account, probably by the end of the day Friday. Instructions on retrieving your exam pdf may be found at: < https://umich.app.box.com/exam-­‐scan-­‐student-­‐guide >. An answer key and a regrade request form are both posted on CTools under resources. Please download the regrade request form and follow the instructions if you request a re-­‐grade or math error correction. Deadline for requests for exam 2 is March 25. 0 50 100 150 200 250 0 To 10 10 To 20 20 To 30 30 To 40 40 To 50 50 To 60 60 To 70 70 To 80 80 To 90 90 To 100 number of students
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Chemistry 215 (Winter 2016) Exam 2 Name: ____________________________ page 1 I. (23 points). Provide the missing products in the following reaction schemes. In all cases, show only the major organic product. The byproducts of the reaction do not need to be shown. H 3 CO O O N CH 3 OCH 3 1) CH 3 MgBr (excess) low temperature 2) H 3 O + workup H 3 CO O O N CH 3 CH 3 1) LiAlH 4 (excess) 2) H 3 O + workup O 1) LDA (1.0 equiv) 2) 3) H 3 O + workup H O 5 5 5 N N O HO O H N O Ph OH NH 2 Ph OPh (1 equiv) SOCl 2 (1 equiv) + 1 equiv pyridine 4 4 (1 equiv) A. B. C. D. ignore stereochemistry show neutral product after pH adjustment OH O HO N +2 if left or right side only is correct +2 if left or right side only is correct O OH +5 O either stereo OK +2 N N O Cl O H N O Ph OH N H Ph OPh N N O O +4 acylation on ROH: +2 no partial correct N-acylation but transcription error elsewhere: +2
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Chemistry 215 (Winter 2016) Exam 2 Name: ____________________________ page 2 II. (27 points).
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