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Chemistry 2412 Exam I: September 27, 2005, Exams of Organic Chemistry

Clayton State UniversityOrganic Chemistry

A chemistry exam consisting of 13 questions worth a total of 100 points. The exam covers various topics such as transformations using reducing agents, internal alkynes, organic products, and ion species. Students are required to identify the correct answers, draw molecules, and propose mechanisms.

Typology: Exams

Pre 2010

Uploaded on 08/04/2009

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Chemistry 2412 Exam I Name ______________________________
September 27, 2005
This exam consists of 13 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 ______________________________ September 27, 2005 This exam consists of 13 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!

September 27, 2005 For questions 1-7 circle the one best answer. (4 points each)

  1. Which of the following transformations could be accomplished by using sodium borohydride as the reducing agent? A. Alkyne to alkane B. Aldehyde to alcohol C. Ester to aldehyde D. Carboxylic acid to aldehyde
  2. What is the major organic product from the following reaction? A. an aldehyde B. a carboxylic acid C. an alcohol D. a ketone
  3. Which of the following reagents should be used to convert an internal alkyne to a diketone? A. KMnO 4 , H 2 O, neutral B. O 3 then H 2 O C. Sia 2 BH then H 2 O 2 D. H 2 O, H 2 SO 4
  4. How many distinct internal alkynes exist with a molecular formula of C 6 H 10 ?. A. 2 B. 3 C. 4 D. 6
  5. Which of the following statements is false? A. cis -3-Chlorocyclohexanol is a tertiary alcohol. B. Alcohols are both weak acids and weak bases. C. 1-Butanol is more soluble in water than 1-decanol. D. 1-Pentanol has a higher boiling point than 2-methyl-2-butanol. HgSO 4 , H 2 O C C H H 2 SO 4

CH 3 CH 2 C CH 3 C C CH 3 CH 2 CH 2 CH 3 H O OH September 27, 2005

  1. (16 points) Name the following molecules: (a) the enol tautomer of (b) (c) (d) The major product of the reaction of 3-hexyne with two molar equivalents of HBr.

  1. excess CH 3 MgBr OCH 3 O O ether

  2. H 3 O+ OH OH Na 2 Cr 2 O 7 H 2 SO 4 HO CH 3 PCC CH 2 Cl 2 September 27, 2005

  3. (16 points) Draw the major product of the following reactions. (a) (b) (c) (d) 2 Na, NH 3 CH 3 CH 2 CH 2 C CCH 3

H C C H H C C CH 3 H 2 Lindlar catalyst Br Mg ether OH H 2 SO 4  September 27, 2005

  1. (14 points) Provide structures or reagents in the empty boxes below to complete the following reaction scheme.