CHEM 1315 Spring 2011 Exam 3 version 2

Name:______________________ Roll Number ________________

Please read the following before proceeding

1. Materials: Turn off cell phones and wireless PDA devices. Place all other materials on the floor. You will only need a pencil. Molecular models are optional. 2. Show your Buzz Card when you turn in your completed exam. 3. You must work alone. 4. This is a closed book exam. Give or take no assistance from other students. Recall the Georgia Tech Honor Code.

"I have always worked better alone."-- Claude Monet I pledge my honor that I have not violated the Honor Code during this examination.

Signed____________________________________________________

Note: A pKa table is provided on the last page.

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CHEM 1315 Spring 2011 Exam 3 version 2

Name:______________________ Roll Number ________________

1. (40 points, 4 points each) Circle the correct answer. There is only one correct answer. a. A) B) C) D) E) b. A) B) C) D) c. A) B) C) D) E) d. A) B) C) D) E) e. Which of the following is not a true statement? Tertiary alcohols undergo SN1 reactions with hydrogen halides. Secondary alcohols undergo SN1 reactions with hydrogen halides. Primary alcohols undergo SN2 reactions with hydrogen halides. Tertiary alcohols undergo E2 dehydration reactions. Secondary alcohols undergo E1 dehydration reactions. Which structure has the poorest leaving group? R-SH R-NH2 R-OH R-Br Which of the following compounds has the best leaving group? an ether an amine an alcohol a protonated alcohol a protonated amine Which of the following anions is the strongest base? fluoride ion (F) carbonate ion (CO32) iodide ion (I) hydroxide ion (OH) acetate ion (CH3CO2) What compound is formed when ethanol is treated with pyridinium chlorochromate (PCC) in dry methylene chloride solvent? A) B) C) D) E) acetic acid (CH3CO2H) acetaldehyde (CH3CHO) ethyl chloride (CH3CH2Cl) Acetone (CH3COCH3) Ethane (CH3CH3)

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CHEM 1315 Spring 2011 Exam 3 version 2

Name:______________________ Roll Number ________________

f.

How many alkyl chlorides can be obtained from monochlorination of the following alkane?

A) B) C) D) g.

1 2 3 6 What is the major product obtained from the monobromination of 2,2,6trimethylheptane?

A) B) C) D) E) h. A) B) C) D) E) i. A) B) C) D) E) j.

2-bromo-2,6,6-trimethylheptane 4-bromo-2,2,6-trimethylheptane 3-bromo-2,2,6-trimethylheptane 1-bromo-2,6,6-trimethylheptane 2-bromo-2,2,6-trimethylheptane Which of the following alkyl halides is the most reactive in an SN2 reaction? 1-bromo-2-methylbutane 2-bromopropane 1-bromopropane 1-bromo-2-methylpropane 1-chlorobutane Which statement best describes a carbon-oxygen bond? The bond is covalent and polar, with oxygen carrying a partial positive charge. The bond is covalent and nonpolar. The bond is ionic and polar, with oxygen carrying a full positive charge. The bond is covalent and polar, with oxygen carrying a partial negative charge. The bond is ionic and polar, with oxygen carrying a full negative charge. What product will be formed from the reaction of trans-1-bromo-4-methylcyclohexane with methoxide ion under SN2 conditions?

A) trans-1-methoxy-4-methylcyclohexane B) trans-4-methylcyclohexanol C) trans- and cis-4-methylcyclohexanol D) cis-1-methoxy-4-methylcyclohexane E) trans- and cis-1-methoxy-4-methylcyclohexane _________/ 20 Page 3 of 8

CHEM 1315 Spring 2011 Exam 3 version 2

Name:______________________ Roll Number ________________

2. (40 points, 4 points each) SHORT ANSWER. Draw the structure, or write the word or phrase that best completes each statement or answers the question. a. What is the starting reactant for the following reaction?

H3C CH CH3

CH3

CH3

Cl2 hv

H3C CH3

Cl

H3C CH3

CH2Cl

b. What is the product of the following reaction under basic conditions?

c. Draw the organic product for the following reaction.

d. Draw the structure of the major product of the following SN2 reaction.

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CHEM 1315 Spring 2011 Exam 3 version 2

Name:______________________ Roll Number ________________

e. Draw the organic product for the following reaction.

f. How many secondary hydrogen atoms are in the following compound?

g. Draw the major product for the following reaction

h. Draw the common product from the following two elimination reactions?

i. Which halide will react more rapidly by an E2 mechanism?

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CHEM 1315 Spring 2011 Exam 3 version 2

Name:______________________ Roll Number ________________

j. What is the product of the following reaction?.

3. (10 points) ) Mechanistic Understanding: Using curved arrows, provide a stepwise mechanism for the reaction of the following diol (4-methyl-1,4-pentandiol) to form a C6H12O product. Also draw the product of the reaction.

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CHEM 1315 Spring 2011 Exam 3 version 2

Name:______________________ Roll Number ________________

4. (10 points) Multistep synthesis: Select one of the following three products. Show how 1-butanol can be converted into any ONE of the following compounds. Provide a sequence of reactions to perform the transformation, showing the reagents and structures of all intermediates products. The synthesis must use the given starting material. You may use any other substrate materials and/or reagents. Do not draw the mechanistic steps.
CH3CH2CH2CH2OCH2CH3 A CH3CH2CH2CH2SH B CH3CH2CH2CH2NH3 C

HBr CH3CH2CH2CH2OH H2SO4 heat heat

CH3CH2O-

CH3CH2CH2CH2OCH2CH3 A SH NH3 CH3CH2CH2CH2NH3 C CH3CH2CH2CH2SH B

CH3CH2CH2CH2Br

HBr

Alternate Routes possible

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CHEM 1315 Spring 2011 Exam 3 version 2

Name:______________________ Roll Number ________________

Write your class roll number on (1) the top of the first page and (2) below. ***** If you need to verify your class roll number, you can do this at the front of the room when you turn in your exam paper. ***** Roll Number _______________ Page 2 (20)________ Page 3 (20)________ Page 4 (16)________ Page 5 (20)________ Page 6 (14)________ Page 7 (10)________ Total 100_________

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