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20 Questions in Exam 1 - Organic Chemistry | CHEM 2325, Exams of Organic Chemistry

Material Type: Exam; Class: Organic Chemistry; Subject: Chemistry; University: University of Texas - El Paso; Term: Fall 2008;

Typology: Exams

Pre 2010

Uploaded on 08/19/2009

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CHEM 2325 Exam 1 Name:
September 25, 2008 UTEP ID #:
You can separate these two sheets to use front and back as your scratch paper. For each reaction assume the
appropriate workup.
1.-5. Match each numbered step of the following synthesis to a mechanism type below. Answers may be
repeated.
Br2
OH Cl
1.
H2SO4, heat
HCl
2.
NaOH, heat
Br-
Br+
Br
OH
O
Br
OH
3.
H2O
4.
NaOH
5.
HBr
a. E1 b. E2 c. SN1 d. SN2 e. not a.-d.
6.-10. Match each set of reagents on the left, reacting with
I
, to its major product on the right.
Answers may be repeated.
6. HI a.
7. heat b.
8. H2O c.
9. Na+-OCH3/HOCH3, heat d.
10. Na+-OC(CH3)3/HOC(CH3)3, heat e. not a.-d.
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CHEM 2325 Exam 1 Name: September 25, 2008 UTEP ID #: You can separate these two sheets to use front and back as your scratch paper. For each reaction assume the appropriate workup. 1.-5. Match each numbered step of the following synthesis to a mechanism type below. Answers may be repeated. Br 2 OH (^) 1. Cl H 2 SO 4 , heat HCl

NaOH, heat Br Br+ - Br Br O OH OH

H 2 O

NaOH

HBr a. E1 b. E2 c. SN 1 d. SN 2 e. not a.-d. 6.-10. Match each set of reagents on the left, reacting with I , to its major product on the right. Answers may be repeated.

  1. HI a.
  2. heat b.
  3. H 2 O c.
  4. Na+-OCH 3 /HOCH 3 , heat d.
  5. Na+-OC(CH 3 ) 3 /HOC(CH 3 ) 3 , heat e. not a.-d.

11.-15. Match each set of reagents on the left, reacting with , to its major product on the right. For chiral products assume racemic mixtures. means a mixture of diastereomers. Keep in mind that any deuterium on oxygen (OD) is easily exchange for hydrogen on hydronium workup. Answers may be repeated.

  1. Hg++^ in H 2 O, NaBD 4 a. OH D
  2. BD 3 , NaO 2 H b. OH D
  3. Cl O O O H , LiAlD 4 c. D OH
  4. BH 3 , NaO 2 H, H 2 CrO 4 , NaBD 4 d. D OH
  5. DCl catalysis in D 2 O e. not a.-d. 16.-20. Match each reaction on the left to its major product on the right. Answers may be repeated.
    • H 2 /Pd a. O
    • HBR 2 + NaO 2 H b.
    • H 2 /Lindlar’s catalyst c. O
    • HgSO 4 /H 2 SO 4 + H 2 O d.
    • Na/NH 3 e. not a.-d. Write your answers on these sheets before transferring them to your Scantron. Nevertheless, your grade will be based solely on your Scantron. These exam sheets will be available after 1 p.m. today in PSCI 202. In the event that a retake is necessary (the class average is below 75 %) I will e-mail you and it will be due next Monday, September 29, by 1 p.m. through http://organic.utep.edu/quiz.