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CHM2210 Practice Set 2

The document contains a practice set for CHM2210, featuring multiple-choice questions, short answer questions, and matching exercises related to organic chemistry concepts such as conformers, stereochemistry, and acid-base definitions. It includes questions on prioritization of functional groups, optical activity, and relationships between compounds. Additionally, it requires drawing structures and mechanisms, as well as identifying chirality centers.

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Ming Yan
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17 views

CHM2210 Practice Set 2

The document contains a practice set for CHM2210, featuring multiple-choice questions, short answer questions, and matching exercises related to organic chemistry concepts such as conformers, stereochemistry, and acid-base definitions. It includes questions on prioritization of functional groups, optical activity, and relationships between compounds. Additionally, it requires drawing structures and mechanisms, as well as identifying chirality centers.

Uploaded by

Ming Yan
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as DOCX, PDF, TXT or read online on Scribd
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CHM2210 Practice Set 2.

1.Which of the following would be has the highest priority according to the sequence rules?
a. —SH c. —CH3
b —NH2 d. —OH

2.(2R,3S)-Dibromobutane is:
a. optically active.
b. racemic.
c. dextrorotatory.
d. a meso compound.
For questions 9 and 10 refer to the diagram below.

3. Which of the following is a gauche conformer?


4. Which of the following is an anti conformer?

5. Which of the following cycloalkanes has the most angle strain?

6. Which of the following is a boat conformation of cyclohexane?

7. Which of the following illustrates an axial OH?

8. Are the two substituents cis or trans?

A. trans
B. cis
C. neither

9. What is the relationship between the following two compounds?

A. Constitutional isomers
B. Stereoisomers
C. Identical
D. Not isomers; different compounds entirely.

10. What is the relationship between the following two compounds?

A. Constitutional isomers
B. Stereoisomers
C. Identical
D. Not isomers; different compounds entirely.

11. For the following reaction, which reactant functions as a base?

a. I; b. II; c. neither

12. A Lewis base is defined as _____.


a. a proton donor
b. an electron pair donor
c. a hydroxide donor
d. an electron pair acceptor

13. A Brønsted-Lowry acid is defined as a ____ and a Brønsted-Lowry base is defined as a ____.
a. proton acceptor, proton donor
b. proton donor, proton donor
c. proton acceptor, proton acceptor
d. proton donor, proton acceptor
e. None of these

14. Identify the relationship between the following two structures.

A. Enantiomers
B. Identical
C. Neither

For Questions 12-15, label each pair of molecules as either:


a. Enantiomers; b. Diastereomers; or c. Identical
15.

16.

17.

18.

True (a)/ False (b)


19. Pairs of enantiomers have the different physical properties.
20. Pairs of enantiomers are easily separated.
21. Diastereomers have different energies.

Matching:
22. _____ is the property of "handedness"; the property of an object that causes it to be
nonsuperimposable on its mirror image.
23. _____ are stereoisomers that are not mirror images.
24. _____ is an atom in a molecule that is bonded to four different atoms or groups of atoms.
25. _____ are molecules which contain chirality centers and a plane of symmetry.
a. chirality center
b. chirality
c. Diastereomers
d. Enantiomers
e. meso compounds

short answer questions


1. Rank the following conformers of the isomers of 1-ethyl-2,4-dimethylcyclohexane from most to
least stable.

2. Consider the molecule 1-Chlorobutane


A) Draw all 7 Newman Projections for the molecule at C1-C2.
B) Label each of the 7 conformers as anti, gauche, or eclipsed
C) Label the most stable conformer
D) Label the least stable conformer

3. A) Draw two chair conformations (ring flip) for trans-1-methyl-4-tertbutylcyclohexane


B) Label the least stable conformation, and provide an explanation as to why it is the least stable.

4. Consider the molecules below. Assign R or S configuration to the molecule shown and Draw its
enantiomer.

a.

b.
5. Draw a diastereomer of the following compound.

6. If a molecule has 3 stereocenters, what is the maximum possible stereoisomers it could have?

7.Assign R, S configurations to each indicated chirality center in the molecules below.

8. Place asterisks at all the chirality centers in each molecule below


a)

b)
9. In the reaction below, label the acid, the base, conjugate acid, and conjugate
base

10. Consider the reaction shown below. Does the equilibrium favor the left or the right?

CH3CH2OH + NO3- CH3CH2O- + HNO3

CH3CH2OH pKa = 16
HNO3 pKa = -1.3

11.Draw the conjugate base of the following compound.

12.Provide a mechanism (arrow pushing) for the reaction below.

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