Chemistry 2412 Exam I February 10, 2005

Name ______________________________

This exam consists of 17 questions on 6 pages. Please write your name at the top of each page. Read all of the questions carefully. If there is anything that is unclear, please ask. Answers should be placed in the spaces provided and written legibly. Be sure to answer all of the questions on the exam. You are allowed to use a model kit. A periodic table is provided on the last page of the exam. The exam is worth 100 points. Each question is labeled with its exact point value. You have one hour and 15 minutes to complete this exam. Exams will be picked up at the end of the class period. No late exams will be accepted. Cheating is not allowed. Anyone caught cheating will be sent to the Judiciary Board for review. Good Luck!

Chemistry 2412 Exam I February 10, 2005

Name _________________________________

For questions 1-7 circle the one best answer. (4 points each) 1. The major organic product from the reaction of 3-methyl-1,3-butanediol with chromium trioxide in sulfuric acid will contain which of the following functional groups? A. B. C. D. One carboxylic acid and one ketone One aldehyde and one ketone One carboxylic acid and one alcohol One carboxylic acid and one aldehyde

2. Which of the following transformations could be accomplished by using LiAlH4 as the reducing agent? A. B. C. D. Alkyne to alkane Ester to alcohol Ester to aldehyde Carboxylic acid to aldehyde

3. What is the major organic product from the following reaction?

2Na NH3 (l)

A.

B.

C.

D.

4. Which of the following reactions will provide the best yield of (S)-2-pentanol? A. B. C. D. (R)-2-pentanol + HBr, followed by treatment with NaOH (R)-2-pentanol + PBr3, followed by treatment with NaOH (R)-2-pentanol + tosyl chloride in pyridine, followed by treatment with NaOH 1-Pentyne + H2O in H2SO4 with HgSO4, followed by reduction with H2 and Raney nickel

5. The reaction of 3-hexyne with two molar equivalents of hydrogen bromide gives which compound as the major product? A. B. C. D. 2,2-dibromohexane 3,3-dibromohexane 3,4-dibromohexane 3-bromo-3-hexene page 2

Chemistry 2412 Exam I February 10, 2005

Name _________________________________

6. Determine the IUPAC name of the following molecule. A. B. C. D. 6-ethyl-2-heptyne 3-methyl-6-octyne 6-methyl-2-octyne 5-methyl-1-heptyne

7. Which of the following statements is false about tert-butyl alcohol? A. B. C. D. It is a tertiary alcohol. It is a weak acid. It is a weak base. It has a higher boiling point than 1-butanol.

8. (4 points) Draw a molecule that is an example of each ot the following. (a) An oxonium ion

(b) A strong base

9. (4 points) Rank the following compounds in order of increasing oxidation level. Place the number rank (1=lowest; 4 = highest) in the blank below the structure.
O H3C C OH H3C CH3 H3C O C H H2C CH2

______

______

______

______

10.

(4 points) Name the following molecule:

CH3 H2C CH C CH3 Br CH C C H

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Chemistry 2412 Exam I February 10, 2005

Name _________________________________

11.

(4 points) Draw the keto tautomer of 1-buten-1-ol.

12. (6 points) The following scheme is proposed for the synthesis of the compound shown below, however, the desired product never forms. Briefly explain why this product will not form.
CH3 CH3CH2CH2C CH 2. 1. NaNH2 CH3 C Br CH3 CH3CH2CH2C C C CH3

13.

(8 points) Draw the major product of the following reactions.

(a)
OH

CH3MgBr ether

OH

(b)
OH

PCC CH2Cl2

page 4

Chemistry 2412 Exam I February 10, 2005

Name _________________________________

14. (12 points) Show the Grignard reagent and carbonyl compounds you would start with to synthesize the following alcohol. List three different possibilities. (You do not need to show formation of the Grignard reagent).
OH CH3 C CH3 CH2

15.

(8 points) Provide all reagents necessary to complete the following transformations.

O

(a)

CH3

CH3

C CH3 OH

(b)
H

page 5

Chemistry 2412 Exam I February 10, 2005

Name _________________________________

16. (12 points) Choose ONE of the following reactions, and draw the major product, showing correct regio- and stereochemistry. Then, propose a complete mechanism for the formation of your product.
H3C OH

HBr

OH

SOCl2 dioxane

page 6

Chemistry 2412 Exam I February 10, 2005

Name _________________________________

17. (10 points) Each of the following conversions requires more than one step. Choose ONE of the following conversions and provide a synthesis, including reagents, to show how this conversion might be accomplished.
O OH

O H C C H

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