Dr. Caroline Clower

Chemistry 2412

2411 Review Worksheet

1. Multiple Choice. Circle the letter that corresponds to the correct answer for each question. There is only one correct answer for each question.

(i) Which of the following molecules have bond angles of approximately 120°?

I. CH4 II. NH3 III. CH2CH2 IV. BH3 V. CO2

A. II, III

B. III, IV

C. III, IV, V

D. II, III, V

(ii) Which of the following bonds is the strongest?

A. C-F B. C-Cl C. C-Br D. C-I

(iii) Which of the following lists of functional groups are correctly ranked in order of priority from highest to lowest?

A. -C(O)CH3 > -CO2H > -CH2OH > -CHO

B. -CO2H > -C(O)CH3 > -CH2OH > -CHO

C. -C(O)CH3 > -CO2H > -CHO > CH2OH

D. -CO2H > -C(O)CH3 > -CHO > -CH2OH

(iv) Which structure has the parent name octane?

A. B.

C. D.

(v) Which of the following has Z stereochemistry?

A. B. C. D.

(vi) Which of the following represents a chrial molecule?

A. B. C. D.

(vii) What R and/or S configuration would be used for the following structure?

A. 3R, 4S

B. 3S, 4S

C. 3R, 4R

D. 3S, 4R

(viii) Which of the following compounds will have the highest boiling point?

A. B.

C. D.

(ix) Which species is the conjugate acid in the following acid-base reaction?

A. B. C. D.

(x) The most stable conformation of (Cl)2CH-CH(Cl)2 is represented by which one of the following Newman projections?

A. B. C. D.

(xi) Which of the following statements is true concerning resonance structures?

A. The arrangement of atoms in all contributing structures must be the same.

B. The arrangement of electrons in all contributing structures must be the same.

C. Each atom in a contributing structure must have a completed valence shell.

D. The contributing structures must have degenerate (equivalent) energies.

(xii) In an SN1 reaction:

A. The stereochemistry of the product is inverted.

B. The stereochemistry of the product is retained.

C. The product is a racemic mixture.

D. There is no control of the stereochemistry.

(xiii) Which of the following is the definition of a pair of enantiomers?

A. Stereoisomers which are non-superimposable mirror images of one another.

B. Stereoisomers which are superimposable mirror images of one another.

C. Stereoisomers which are not mirror images of one another.

D. Isomers with the same molecular formula but different connectivity.

(xiv) Arrange the following isomeric alkenes in order of increasing stability (low<high).

I. 2-Methyl-1-pentene

II. 1-Hexene

III. 2-Methyl-2-pentene

IV. 2,3-Dimethyl-2-butene

A. I<IV<II<III

B. II<III<I<IV

C. II<I<III<IV

D. II<I<IV<III

2. Short Answer.

(i) Draw the major organic products that are produced upon the solvolysis of isopropyl chloride with ethanol.

(ii) Draw a valid resonance structure for the following molecule.

(iii) Draw the most stable chair conformation of trans-1,4-dimethylcyclohexane.

(iv) Draw the major organic product for the following reaction.

(v) What is the relationship between the following two structures (enantiomers, diastereomers, or identical molecules)?

(vi) Draw three constitutional isomers with the molecular formula C3H9N.

(vii) Draw the most stable carbocation with the molecular formula C5H11+, clearly showing the location of the cationic charge.

(viii) Draw a molecule that can act as both a Brønsted-Lowry acid and a Brønsted-Lowry base.

(ix) What reaction conditions are required in order for N-bromosuccinimide to react with an alkene?

(x) For each of the following reactions predict whether the predominate mechanism(s) will be SN1, SN2, E1, or E2. (You do not need to draw the products, just tell me which mechanism(s) will most likely occur for each reaction. There may be more than one mechanism per reaction.)

(4)

3. Draw a complete mechanism (including arrows, intermediates, and all appropriate stereochemistry) for the following reaction.

4. Draw an energy diagram for the following elimination reaction on the graph provided.

(a) Label the activation energy for the rate-determining step on the diagram.

(b) Label the heat of reaction on the diagram.

(d) Is the reaction E1 or E2?

5. On the molecule below, label an example of each of the following:

(a) an sp2 hybridized oxygen

(b) an sp3 hybridized carbon

(d) a tertiary carbon

(e) a carboxylic ester