Download 4 Questions on Organic Chemistry - Practice Test 1 | CHEM 231A and more Exams Organic Chemistry in PDF only on Docsity!
Name: Whittier College
Organic Chemistry: CHEM 231A
Test # 1
125 Points Total February 24, 2003
- Answer the following questions: (28 points – 7 pts each) 1a. In regards to alcohols, what is meant by the term amphoteric? Explain briefly and provide a sufficient number of specific example reactions to assist in making your point.
1b. Compare and contrast the physical properties of alcohols to alkanes. What accounts for these physical properties? Explain briefly
1c. What is a grignard reagent? Briefly explain why it reacts the way it does.
1d. What is the difference between a retrosynthetic analysis and a synthesis? Explain briefly.
- Consider the following reactions. Provide an answer that satisfies the question mark: Either predict one
major product for each reaction OR provide the reagents for each synthesis (more than one reaction may be required). Extremely briefly explain your rationale: (40 points – 8 points for each)
HO
OH
2a.
2b.
2c.
2d.
2e.
OH
MgBr
Br
Et 2 O
- CH 3 Br / Et 2 O
- Aqueous Workup
O O S
O
O
HO 1. Mg / Et^2 O
- O H
OH OH (^) Na 2 Cr 2 O 7 (excess)
H 2 SO 4 / H 2 O
O OH O
? H
- Bob wanted to conduct the following reaction: (24 points)
O H O
O
- / Et 2 O / -78 C
- Aqueous Work-up
MgBr O
O
OH
4a. How would he specifically use spectroscopy (NMR, IR, & GC-MSD) to determine whether this reaction occurred as predicted? Provide specific and complete NMR data, pertinent IR data and the important GC-MSD data that would provide proof that this reaction occurred. (17 points)
4b. What would you predict the product(s) would be if this reaction were done at room temperature. That is, what is the relevance of the temperature for this experiment? Explain Briefly. (7 points)
Extra Credit (5 points = don’t even think about doing this until you have finished the rest of the test!!!) If an excess of the Grignard reagent were added to the molecule, what would the product be? Explain briefly.
