CHEMISTRY 2211
Spring 2025, Exam 3
Name: _________KEY____________________________
U-number: ______________
Section: ________________
This exam is administered under the USF Honor Code.
Signature: __________________________
Directions:
• Do not open or begin this exam until instructed.
• The exam has a total of 130 points (125 + 5 extra credit) and includes 20 questions.
• Only legible answers written on the exam will be considered for grading.
• Notes, textbooks, and unauthorized materials are not permitted.
Test taking tips:
• Flip through exam to get a feel for the length and questions.
• Do the questions you know first. Then attempt harder questions.
• Use your time wisely. Don’t get stuck on one section.
• READ QUESTIONS CAREFULLY.
• Show your work; partial credit may be awarded.
Grading:
Page 2 _________ out of 10
Page 3 _________ out of 11
Page 4 _________ out of 22
Page 5 _________ out of 10
Page 6 _________ out of 20
Page 7 _________ out of 15
Page 8 _________ out of 20
Page 9 _________ out of 13
Page 10 _________ out of 9
TOTAL ________ out of 130
1
, 1. Which of the following structures represents a hemiacetal. Circle your answer (2 points)
2. Which of the following methods would NOT yield an aldehyde as its major product?
Circle your answer (2 points)
A) Reaction of a primary alcohol with PCC
B) Reaction of cyclopentene with O3 followed by (CH3)2S
C) Hydroboration–Oxidation of but-1-yne
D) Reaction of an ester with DIBAH followed by acidic workup.
E) Reaction of an acid chloride with excess CH3MgBr followed by acidic workup
3. Which of the following reagents could NOT be used to carry out the transformation shown?
Circle your answer (2 points)
A) LiAlH4, ether
B) Zn(Hg), HCl, heat
C) (1) NH2NH2/H+; ( 2) KOH/H2O/heat
D) (1) HSCH2CH2SH, H+; (2) Raney Ni
4. Which of the following reagents could be used to carry out the transformation shown?
Circle your answer (2 points)
A) NaCl
B) Cl2
C) KOCl
D) SOCl2
5. Which of the following structures has the highest reactivity towards nucleophilic acyl
substitution. Circle your answer (2 points)
2
Spring 2025, Exam 3
Name: _________KEY____________________________
U-number: ______________
Section: ________________
This exam is administered under the USF Honor Code.
Signature: __________________________
Directions:
• Do not open or begin this exam until instructed.
• The exam has a total of 130 points (125 + 5 extra credit) and includes 20 questions.
• Only legible answers written on the exam will be considered for grading.
• Notes, textbooks, and unauthorized materials are not permitted.
Test taking tips:
• Flip through exam to get a feel for the length and questions.
• Do the questions you know first. Then attempt harder questions.
• Use your time wisely. Don’t get stuck on one section.
• READ QUESTIONS CAREFULLY.
• Show your work; partial credit may be awarded.
Grading:
Page 2 _________ out of 10
Page 3 _________ out of 11
Page 4 _________ out of 22
Page 5 _________ out of 10
Page 6 _________ out of 20
Page 7 _________ out of 15
Page 8 _________ out of 20
Page 9 _________ out of 13
Page 10 _________ out of 9
TOTAL ________ out of 130
1
, 1. Which of the following structures represents a hemiacetal. Circle your answer (2 points)
2. Which of the following methods would NOT yield an aldehyde as its major product?
Circle your answer (2 points)
A) Reaction of a primary alcohol with PCC
B) Reaction of cyclopentene with O3 followed by (CH3)2S
C) Hydroboration–Oxidation of but-1-yne
D) Reaction of an ester with DIBAH followed by acidic workup.
E) Reaction of an acid chloride with excess CH3MgBr followed by acidic workup
3. Which of the following reagents could NOT be used to carry out the transformation shown?
Circle your answer (2 points)
A) LiAlH4, ether
B) Zn(Hg), HCl, heat
C) (1) NH2NH2/H+; ( 2) KOH/H2O/heat
D) (1) HSCH2CH2SH, H+; (2) Raney Ni
4. Which of the following reagents could be used to carry out the transformation shown?
Circle your answer (2 points)
A) NaCl
B) Cl2
C) KOCl
D) SOCl2
5. Which of the following structures has the highest reactivity towards nucleophilic acyl
substitution. Circle your answer (2 points)
2
