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Chemistry 2412 Exam I: Organic Chemistry, Exams of Organic Chemistry

Clayton State UniversityOrganic Chemistry

A chemistry exam consisting of 17 questions worth a total of 100 points. The exam covers various organic chemistry topics such as functional groups, organic reactions, and synthesis. Students are required to identify functional groups, predict organic reactions, and draw structures of molecules. The exam includes multiple-choice questions, drawing questions, and synthesis problems.

Typology: Exams

Pre 2010

Uploaded on 08/04/2009

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koofers-user-5k8 🇺🇸

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Chemistry 2412 Exam I Name ______________________________
February 10, 2005
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!
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Chemistry 2412 Exam I Name ______________________________ February 10, 2005 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!

February 10, 2005 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. One carboxylic acid and one ketone B. One aldehyde and one ketone C. One carboxylic acid and one alcohol D. One carboxylic acid and one aldehyde
  2. Which of the following transformations could be accomplished by using LiAlH 4 as the reducing agent? A. Alkyne to alkane B. Ester to alcohol C. Ester to aldehyde D. Carboxylic acid to aldehyde
  3. What is the major organic product from the following reaction? A. B. C. D.
  4. Which of the following reactions will provide the best yield of ( S )-2-pentanol? A. ( R )-2-pentanol + HBr, followed by treatment with NaOH B. ( R )-2-pentanol + PBr 3 , followed by treatment with NaOH C. ( R )-2-pentanol + tosyl chloride in pyridine, followed by treatment with NaOH D. 1-Pentyne + H 2 O in H 2 SO 4 with HgSO 4 , followed by reduction with H 2 and Raney nickel
  5. The reaction of 3-hexyne with two molar equivalents of hydrogen bromide gives which compound as the major product? A. 2,2-dibromohexane B. 3,3-dibromohexane C. 3,4-dibromohexane D. 3-bromo-3-hexene NH 3 ( l ) 2 Na

CH 3 MgBr OH O O ether OH OH PCC CH 2 Cl 2 February 10, 2005

  1. (4 points) Draw the keto tautomer of 1-buten-1-ol.
  2. (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.
  3. (8 points) Draw the major product of the following reactions. (a) (b)
    1. NaNH 2 CH 3 CH 2 CH 2 C CH
  4. C Br CH 3 CH 3 CH 3 CH 2 CH 2 C C C CH 3 CH 3

CH 3 C CH 2 CH 3 OH H H CH 3 C OH O CH 3 C C CH 3 February 10, 2005

  1. (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).
  2. (8 points) Provide all reagents necessary to complete the following transformations. (a) (b)

OH O H C C H H O February 10, 2005

  1. (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.