Name:
Whittier College
Organic Chemistry: CHEM 231B
Test # 1
115 Points Total
February 24, 2004
1. Multiple Choice Questions: Circle the letter corresponding to the single, most appropriate answer.
(15 points = 3 pts each)
1a. Which of the following methyl groups will exhibit the highest chemical shift in 1H-NMR spectroscopy?
a) methyl amine
b) methanol
c) acetone (2-propanone)
d) propane
e) methylbenzene (toluene)
1b. How many proton NMR singlets will 2-bromo-3-methyl-2-butene exhibit?
a) 1
b) 2
c) 3
d) 4
e) 0
1c. Which of the following alkenes reacts with aqueous hydrochloric acid at the slowest rate?
a) 3-methyl-1-butene
b) 2-methyl-1-butene
c) 2-methyl-1-pentene
d) 2-methyl-2-butene
e) 2,3-dimethyl-2-pentene
1d. Which of the following electromagnetic waves are used in NMR Spectroscopy?
a) X-ray
b) infrared
c) ultraviolet
d) radio
e) microwave
1e. What is the major product for the reaction of 1-methylcyclopentene with hydrochloric acid?
a) 1-chloromethylcyclopentene
b) 1-chloro-1-methylcyclopentane
c) 1-chloro-2-methylcyclopentane
d) 1-chlorocyclohexane
e) 1-chloro-2-methylcyclopentene
2. Provide answers to the following questions: (24 pts total = 8 pts each)
2a. Why does coupling exist in NMR spectroscopy? Explain in both general and specific terms.
2b. What is IR Spectroscopy? What information does it provide for us? Briefly explain the theory behind
it.
2c. What is the structure/shape of an alkene? Draw it. How does this structure explain the reactivity of
alkenes? Explain briefly.
3. Consider the following reactions. Predict the single MAJOR product and briefly explain your answer.
Mechanisms are NOT required, but may be used. Pay close attention to stereochemical issues: (24
points – 8 points for each)
