CHEM 120 Exam 2 F19 KEY

CHEM 120 (Hamann) Exam 2 Name: ,
Last First

Part I /60
Total of 137 exam points, adjusted to 100 course points.
Part II /39
ADJUSTED SCORE:
Part III /38

Part I: Multiple Choice (3 points each, 60 pts total, No guessing correction, so answer ALL questions)
Note, only questions that are marked as such might have multiple correct answers.
Use the following answers for Numbers 1-24 (12 questions)
AA: Alkanes AB: Alkenes AC: Alkynes AD: Aromatics AE: Alkyl Halides
BA: 1o Alcohols BB: 2o Alcohols BC: 3o Alcohols BD: 1o Amines BE: 2o Amines
CA: 3o Amines CB: 4o Ammonium Salts CC: Aldehydes CD: Ketones
CE: Hemiacetals DA: Acetals DB: Carboxylic Acids DC: Esters DD: 1o Amides
DE: 2o amides EA: 3o Amides EB: Phenols EC: Ethers ED: Thiols
EE: Monosulfides EC: Disulfides


To answer these questions requires two lines on the Scantron, one for each letter of the answer. For example:
1-2. Which functional group results in the smelliest compounds?
The answer is ED: Thiols. Therefore, you would bubble in E on line 1 on the Scantron, and D on line 2.
The order matters (answering DE would be wrong, as that would indicate your answer is 2 o amide which is
wrong), and both lines are graded together as a single question. Answer this question now on lines
1-2 to get credit for this question.
3-4. Which functional group has a carbonyl group attached to both a carbon and to a hydrogen? CC:
Aldehyde
5-6. Which functional group is made by the gentle oxidation of a thiol? EC: Disulfides
7-8. Which functional group is the condensation product of a 2 o amine and a carboxylic acid? EA: 3o Amides
9-10. Which functional group is the most acidic? DB: Carboxylic Acids (phenol common wrong answer)
11-12. Which functional group undergoes saponification? DC: Esters
13-14. Which functional group give compounds the highest boiling point? DD: 1o Amides
15-16. Which functional groups has a set of carbon-carbon double bonds with unusual stability? AD: Aromatics
17-18. Which functional group promotes more soluble in aq NaOH than in water, but not more solubility in aq
NaHCO3? EB: Phenols - carboxylic acid common wrong answer, but they are more soluble in
NaHCO3 ; thiol would also be correct, and credit was given to those (who guess this?)
19-20. Reduction of which functional group gives a 2o alcohol? CD: Ketone
21-22. Which functional group is most unstable in water? CE: Hemiacetals
23-24. Which of these functional groups reacts with acid to form a salt but cannot make an amide?
CA: 3o Amines
25. The compound on the right would be classified as
A) an aromatic amine CH3
H3C
B) a primary amine CH3
C) a secondary amine H 3C N
H
D) a tertiary amine
E) a quaternary amine
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, 26. Which of the following is an alternate name for 2-methyl-1-propoxypropane?
A) butyl propyl ether
B) sec-butyl propyl ether
C) isobutyl isopropyl ether
D) sec-butyl sec-propyl ether
E) isobutyl propyl ether

27. Which of the following is the best name for the compound on the right?
A) 3,4-dichlorobenzaldehyde
B) 4,5-dichlorobenzaldehyde
C) 3,4-dichlorophenylaldehyde
D) 1,2-dichlorobenzenaldehyde
E) 3,4-dichlorobenzenaldehyde


28. Which of the following structures is a hemiacetal derived from an ketone? B
A B C D E
O O O OH O O OH O O




29. For the following reaction, which of the following changes would shift the equilibrium to the right? Mark all
that apply.
CH3CH=CH2 + H2O D CH3CHOHCH3 + heat
A) Using a smaller reaction flask
B) Decreasing the amount of CH3CH=CH2
C) Decreasing the amount of CH3CHOHCH3
D) Decreasing the amount water
E) Stirring the reaction faster


30. The best name for the compound on the right is
CH3 CH2 CH3
A) 2,4-diethyl-2-methyl-3-pentanol
B) 3,3,5-trimethylheptanol H3C C CH CH CH3
C) 5-ethyl-3,3-dimethyl-4-hexanol
D) 2-ethyl-4,4-dimethyl-3-hexanol CH3 CH2 OH
E) 3,3,5-trimethyl-4-heptanol


31. Hemiacetals are usually not stable and revert to the alcohol and the aldehyde or ketone they were made
from. Which of the following hemiacetals would be the most stable? Compound A (CYCLIC)




32. What bond angles does VSEPR predict for the carbon in formaldehyde (H2C=O)?
Hint: Draw the structure!
A) 60o B) 90o C) 109.5o D) 120o E) 180o


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