CHM1321 C Midterm 1 2018 Page 2 of 11
Part A B C Bonus Total
Points 10 20 20 3 50
Mark
TA
Part A – 1 or 2 points per question
1. The molecule below is Aspartame, a common sugar replacement found in low-calorie
drinks and other products.
hybridization = sp3
amide geometry = tetrahedral
O
O O
carboxylic acid H N ester
O NH 2 H O
amine
a. (2 pts) Circle and identify the functional groups present in Aspartame.
b. (0.5 pt) Give the hybridization and geometry of the atom indicated with an arrow.
2. (2.5 pts) Give the line structure or the IUPAC names for the following compounds:
STRUCTURE NAME
Z-3-isopropyl-7-methyl-1,6-nonadiene
Z-3-isopropyl-7-methyl-nona-1,6-diene
Z-7-methyl-3-isopropyl-1,6-nonadiene
trans-1-ethyl-2-tert-butyl-cyclopentane
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, CHM1321 C Midterm 1 2018 Page 3 of 11
3. (0.5 pt) Out-of-phase head-on overlap of atomic orbitals creates anti-bonding π
molecular orbitals.
TRUE FALSE (should be “side-on overlap”)
4. (0.5 pt) Which of the following solvents should be capable of dissolving ionic
compounds? (must be polar to dissolve a salt – LIKE DISSOLVES LIKE)
Liquid SO2 Liquid NH3 Benzene Tetrachloromethane
5. (1.5 pts) Circle the chiral molecule(s) and underline the meso compound(s).
H
Br OH OH
H
O Cl
H
6. (0.5 pt) Rank the following compounds in order from least (1) to most (3) acidic.
O O O
H 3C CH 3 H 3C CH 3 H 3C CH 3
O O O O O O
H H H H H H
2 1 3
7. (1 pt) Using the electron-pushing arrows as a guide, draw the expected product(s) of the
following reaction.
H
1 O
5 3
H 1 H
H 2N O 2 6 N H
6 4 2
3
5
4
8. (1 pt) Add lone pairs and electron-pushing arrows as needed to complete the following
reaction:
O O O O
+ H
This study source was downloaded by 100000858936669 from CourseHero.com on 02-06-2023 05:23:01 GMT -06:00
https://www.coursehero.com/file/31418896/KEY-2018-Midterm-1pdf/
Part A B C Bonus Total
Points 10 20 20 3 50
Mark
TA
Part A – 1 or 2 points per question
1. The molecule below is Aspartame, a common sugar replacement found in low-calorie
drinks and other products.
hybridization = sp3
amide geometry = tetrahedral
O
O O
carboxylic acid H N ester
O NH 2 H O
amine
a. (2 pts) Circle and identify the functional groups present in Aspartame.
b. (0.5 pt) Give the hybridization and geometry of the atom indicated with an arrow.
2. (2.5 pts) Give the line structure or the IUPAC names for the following compounds:
STRUCTURE NAME
Z-3-isopropyl-7-methyl-1,6-nonadiene
Z-3-isopropyl-7-methyl-nona-1,6-diene
Z-7-methyl-3-isopropyl-1,6-nonadiene
trans-1-ethyl-2-tert-butyl-cyclopentane
This study source was downloaded by 100000858936669 from CourseHero.com on 02-06-2023 05:23:01 GMT -06:00
https://www.coursehero.com/file/31418896/KEY-2018-Midterm-1pdf/
, CHM1321 C Midterm 1 2018 Page 3 of 11
3. (0.5 pt) Out-of-phase head-on overlap of atomic orbitals creates anti-bonding π
molecular orbitals.
TRUE FALSE (should be “side-on overlap”)
4. (0.5 pt) Which of the following solvents should be capable of dissolving ionic
compounds? (must be polar to dissolve a salt – LIKE DISSOLVES LIKE)
Liquid SO2 Liquid NH3 Benzene Tetrachloromethane
5. (1.5 pts) Circle the chiral molecule(s) and underline the meso compound(s).
H
Br OH OH
H
O Cl
H
6. (0.5 pt) Rank the following compounds in order from least (1) to most (3) acidic.
O O O
H 3C CH 3 H 3C CH 3 H 3C CH 3
O O O O O O
H H H H H H
2 1 3
7. (1 pt) Using the electron-pushing arrows as a guide, draw the expected product(s) of the
following reaction.
H
1 O
5 3
H 1 H
H 2N O 2 6 N H
6 4 2
3
5
4
8. (1 pt) Add lone pairs and electron-pushing arrows as needed to complete the following
reaction:
O O O O
+ H
This study source was downloaded by 100000858936669 from CourseHero.com on 02-06-2023 05:23:01 GMT -06:00
https://www.coursehero.com/file/31418896/KEY-2018-Midterm-1pdf/
