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HW3 - Question 4 Calicene(structure below has a...

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CHEM 2312: Homework 3 Due February 4th, 2005 Note: An answered hardcopy must be submitted to Dr. AJ Ragauskas; all 4 questions must be answered. Question 1. (6 points) Arrange the following products according to the % yield obtained from the nitration of t-butylbenzene. Justify the order (6 points) NO 2 NO 2 O 2 N 1a 1 b 1c
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CHEM 2312: Homework 3 Student Name_________________________ Due Sept. 15, 2003(1:00 pm) Student ID:____________________________ Question 2. (4 marks) What is the structure of the compound that has the 1 H-NMR spectrum shown below? CH 2 CH 2 CH O CH 2 CCH 3 O C H 3 C CH 3 O CCH 2 CH 3 O 2a 2b 2c 2d Question 3. On heating 1,2,4,5-tetramethylbenzene with fuming sulfuric acid one product is isolated with the molecular formula of C 10 H 14 O 3 S in 94% yield. Identify the structure of the product and provide a reasonable reaction mechanism for the product. (8 points)
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Unformatted text preview: Question 4. Calicene (structure below) has a surprisingly large dipole for a hydrocarbon. (a) Provide the structure of a major ( i.e. stable) resonance contributor that explains the polarity. (b) Provide a brief ( one sentence ) explanation that accounts for the stability of the resonance structure that you have drawn. (5 points) TMS 12 18 12 18 triplet quartet Chemistry 2312 Homework 3 Answer Form – Due February 4th, 2005 Student Name: __________________Class Roll Number: _______________ Answer Question 1 Highest Yield: __________ ; 2 nd Highest Yield_________; Lowest Yield: __________ Justification: Question 2 Question 3 Question 4 Major Resonance Structure: Question 4 Explanation...
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