CHEM 222 (Hamann) Exam 3 Name:
Please circle your family (last) name
Part I /50
Total of 179 exam points, adjusted to 100 course points. ADJUSTED SCORE:
Part II /57
Part III /30
Part IV /42
Pa
Part
rt I: T
Topics
opics from Exam 1 & 2
1. (20 pts) ID functional groups and some easy stereochemistry
2. (12 pts) Draw all reasonable resonance structures for the following species. New structure, but similar to
previous.
3. (8 pts) Convert the following to a Newman Projection with the bold bond as the central axis, or to a Line
Structure, as indicated. Note the possible stereochemical relationships for both compounds.
4. (10 pts) Add arrows to indicate how the following reaction sequence progresses. (Remember, arrows only show
what the electrons are doing.)
Pa
Part
rt II: Reactions (3 pts each arrow, 57 pts total) For each of the following, give the product(s) as indicated, or the
starting material or reagent, if missing. If more than one starting material is given, show only the product of
the more reactive starting material under the reaction conditions given. NR (no reaction) is a possible answer.
5-18. (alphabetical list)
cycloalkene addition reaction with stereo- and regiochemistry
E1
E2 reaction with stereochemistry
Product of a 2-reaction sequence
reaction with rearrangement
reagents for 2-step conversion
reagents for 2-step conversion
reagents for 2-step conversion
reagents for diol formation with stereochemistry
reagents for diol formation with stereochemistry
SN1
SN2
SN2
Stereochemistry of E2
Pa
Part
rt III: Mechanistic Understanding
19. (30 pt) Question about 2 reactions, potential energy curves, transition states, and Hammond's Postulate.
Pa
Part
rt IV
IV:: Mass Spectroscopy
20. (9 pts) Uniques characteristics seen in some mass spectra.
21. (6 pts) Common mass loss pattern in MS
22. (5 pts) Different types of MS
23. (10 pts) Differentiating similar compounds by MS
24. (12 pts) Predicting the standard fragmentation of a radical cation
Please circle your family (last) name
Part I /50
Total of 179 exam points, adjusted to 100 course points. ADJUSTED SCORE:
Part II /57
Part III /30
Part IV /42
Pa
Part
rt I: T
Topics
opics from Exam 1 & 2
1. (20 pts) ID functional groups and some easy stereochemistry
2. (12 pts) Draw all reasonable resonance structures for the following species. New structure, but similar to
previous.
3. (8 pts) Convert the following to a Newman Projection with the bold bond as the central axis, or to a Line
Structure, as indicated. Note the possible stereochemical relationships for both compounds.
4. (10 pts) Add arrows to indicate how the following reaction sequence progresses. (Remember, arrows only show
what the electrons are doing.)
Pa
Part
rt II: Reactions (3 pts each arrow, 57 pts total) For each of the following, give the product(s) as indicated, or the
starting material or reagent, if missing. If more than one starting material is given, show only the product of
the more reactive starting material under the reaction conditions given. NR (no reaction) is a possible answer.
5-18. (alphabetical list)
cycloalkene addition reaction with stereo- and regiochemistry
E1
E2 reaction with stereochemistry
Product of a 2-reaction sequence
reaction with rearrangement
reagents for 2-step conversion
reagents for 2-step conversion
reagents for 2-step conversion
reagents for diol formation with stereochemistry
reagents for diol formation with stereochemistry
SN1
SN2
SN2
Stereochemistry of E2
Pa
Part
rt III: Mechanistic Understanding
19. (30 pt) Question about 2 reactions, potential energy curves, transition states, and Hammond's Postulate.
Pa
Part
rt IV
IV:: Mass Spectroscopy
20. (9 pts) Uniques characteristics seen in some mass spectra.
21. (6 pts) Common mass loss pattern in MS
22. (5 pts) Different types of MS
23. (10 pts) Differentiating similar compounds by MS
24. (12 pts) Predicting the standard fragmentation of a radical cation
