310NSu10Exam2Key

310NSu10Exam2Key - LastName: FirstName: CH310N Espaa...

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Last Name: First Name: DO ALL QUESTIONS!!! GOOD LUCK ON THE EXAM!!! CH 310N España Summer 2010 Dr. Brian M. Bocknack Midterm Exam #2 Friday, August 6, 2010 9:00–11:00 a.m. PLEASE DO NOT OPEN THIS EXAM BOOKLET UNTIL YOU ARE TOLD TO DO SO!!! Exam results and the answer key will be available in Blackboard on Sunday, August 8 after 12:00 p.m. Enjoy the excursion to Pamplona, and then worry about how you did on the exam! Your exam raw score (out of 300) is calculated below. Your curved exam grade (T score) on a 100 point scale is listed below the raw score. This exam is worth 27.5% of your final course grade. Page Page Page 2 (20) 6 (30) 10 (46) 3 (24) 7 (22) 11 (27) 4 (20) 8 (16) 12 (30) 5 (28) 9 (37) Total (300) (100) T Score Including this cover page, this exam contains 12 pages. The pK a data, spectroscopic data, periodic table, Organic I reaction summary, and scratch paper will be provided separately.
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PLEASE READ EVERY QUESTION VERY CAREFULLY!!! Bocknack CH 310N/Summer 2010/Midterm Exam #2 Page 2 1. (4 points) Rank the compounds below according to increasing reactivity toward nucleophilic addition . 1 = least reactive toward nucleophilic addition; 3 = most reactive toward nucleophilic addition KETONES ARE LESS REACTIVE THAN ALDEHYDES; REACTIVITY IS GREATER WHEN EWG IS CLOSER TO CARBONYL C 2 1 3 2. (4 points) Rank the compounds below according to increasing solubility in water. 1 = least soluble in water ; 3 = most soluble in water Page Total MORE H BONDING = MORE SOLUBLE 3 2 1 3. (4 points) Rank the compounds below according to increasing pH . The most acidic proton in each structure is circled. 1 = lowest pH; 3 = highest pH 3 LOWEST pH = STRONGEST ACID 2 1 4. (4 points) Rank the compounds below according to increasing strength of the C=O bond. 1 = weakest C=O bond; 3 = strongest C=O bond MORE IMPORTANT RESONANCE = WEAKER C=0 BOND 1 3 2 5. (4 points) Rank the compounds below according to increasing reactivity toward nucleophilic acyl substitution. 1 = least reactive toward nucleophilic acyl substitution; 3 = most reactive toward nucleophilic acyl substitution BETTER LEAVING GROUP = MORE REACTIVE IN NUCLEOPHILIC ACYL SUBSTITUTION 2 3 1 Continued on Page 3…
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PLEASE READ EVERY QUESTION VERY CAREFULLY!!! Bocknack CH 310N/Summer 2010/Midterm Exam #2 Page 3 Class challenge : If everybody earns a perfect score on this page, there WILL NOT be any nomenclature questions on the final exam! In Questions 6 through 8, draw a line-angle structure corresponding to each name. Write your answer in the empty box provided. Please only show hydrogen atoms that are bonded directly to a hetereoatom , or that are bonded directly to a carbonyl carbon atom . 6. (4 points) 3-Oxocyclohexanecarboxylic acid 7. (4 points) tert -Butyl benzoate 8. (4 points) N -Ethyl-4-methylpentanamide In Questions 9 through 11, provide the IUPAC name for the compound shown. Write your answer in the empty box provided. Be sure to indicate the stereochemistry in your answer for Q10!!!
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This note was uploaded on 10/25/2010 for the course CH 310n taught by Professor Iverson during the Summer '08 term at University of Texas.

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310NSu10Exam2Key - LastName: FirstName: CH310N Espaa...

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