CONFIDENTIAL HAND IN
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Turn in exam question paper Answers recorded on exam paper
Page 1 of 18 pages
Tutorial Section Number _______
Name: ___________________________ Student Number: _____________________
QUEEN’S UNIVERSITY FINAL EXAMINATION
FACULTY OF ARTS & SCIENCE
DEPARTMENT OF CHEMISTRY
CHEM/ENCH 222 – Professor Lucia Lee
April 9, 2025
INSTRUCTIONS TO STUDENTS:
This examination is 3 HOURS in length.
There are 3 sections to this examination.
Please answer all questions in the exam.
The following aids are allowed:
Casio FX-991 calculator
Put your student number on all pages including the front.
GOOD LUCK!
PLEASE NOTE:
Proctors are unable to respond to queries about the interpretation of exam questions.
Do your best to answer exam questions as written.
This material is copyrighted and is for the sole use of students registered in CHEM/ENCH 222
and writing this exam. This material shall not be distributed or disseminated. Failure to abide by
these conditions is a breach of copyright and may also constitute a breach of academic integrity
under the University Senate's Academic Integrity Policy Statement.
,Name: ___________________________ Student Number: _____________________
2 of 18 pages
Long Answer Questions (Total of 3)
1. The IR, EI-MS and NMR (1H and 13C) data of an unknown organic compound containing two
oxygens are shown below. Propose a possible structure. (23.5 marks)
a) IR Analysis
1738
Label Functional Bond Expected Observed U
Group (Vibrational Frequency Range Frequency (cm-1)
mode) (cm-1)
/5
, Name: ___________________________ Student Number: _____________________
3 of 18 pages
b) MS analysis (Be specific with isotopes)
EI-MS (m/z) significant fragments: M.+(180 and 182 have a relative intensity ratio of 100/98), 149/151,
121/123 and 74.
/6.5
1
Turn in exam question paper Answers recorded on exam paper
Page 1 of 18 pages
Tutorial Section Number _______
Name: ___________________________ Student Number: _____________________
QUEEN’S UNIVERSITY FINAL EXAMINATION
FACULTY OF ARTS & SCIENCE
DEPARTMENT OF CHEMISTRY
CHEM/ENCH 222 – Professor Lucia Lee
April 9, 2025
INSTRUCTIONS TO STUDENTS:
This examination is 3 HOURS in length.
There are 3 sections to this examination.
Please answer all questions in the exam.
The following aids are allowed:
Casio FX-991 calculator
Put your student number on all pages including the front.
GOOD LUCK!
PLEASE NOTE:
Proctors are unable to respond to queries about the interpretation of exam questions.
Do your best to answer exam questions as written.
This material is copyrighted and is for the sole use of students registered in CHEM/ENCH 222
and writing this exam. This material shall not be distributed or disseminated. Failure to abide by
these conditions is a breach of copyright and may also constitute a breach of academic integrity
under the University Senate's Academic Integrity Policy Statement.
,Name: ___________________________ Student Number: _____________________
2 of 18 pages
Long Answer Questions (Total of 3)
1. The IR, EI-MS and NMR (1H and 13C) data of an unknown organic compound containing two
oxygens are shown below. Propose a possible structure. (23.5 marks)
a) IR Analysis
1738
Label Functional Bond Expected Observed U
Group (Vibrational Frequency Range Frequency (cm-1)
mode) (cm-1)
/5
, Name: ___________________________ Student Number: _____________________
3 of 18 pages
b) MS analysis (Be specific with isotopes)
EI-MS (m/z) significant fragments: M.+(180 and 182 have a relative intensity ratio of 100/98), 149/151,
121/123 and 74.
/6.5
