Final Exam Answers: Previous Exams

9.6 #4

Classify the following by identifying them as acetals, hemiacetals, or neither.

9.5

Complete the following reaction scheme by filling in the missing structures and reagents.

6.15 c

Complete the following table, filling in the missing major product(s), reagents/conditions, and/or starting material.

6.15 d

Complete the following table, filling in the missing major product(s), reagents/conditions, and/or starting material.

6.15 e

Complete the following table, filling in the missing major product(s), reagents/conditions, and/or starting material.

7.8 b

Complete the following table, filling in the missing major product(s), reagents/conditions, and/or starting material.

7.8 d

Complete the following table, filling in the missing major product(s), reagents/conditions, and/or starting material.

8.9 b

Complete the following table, filling in the missing major product(s), reagents/conditions, and/or starting material.

4.5 c

Complete the following table, filling in the missing major product(s), reagents/conditions, starting material and/or name of the reaction as shown in the example.

4.5 e

Complete the following table, filling in the missing major product(s), reagents/conditions, starting material and/or name of the reaction as shown in the example.

4.5 f

Complete the following table, filling in the missing major product(s), reagents/conditions, starting material and/or name of the reaction as shown in the example.

4.3 #6

Complete the following table, filling in the missing major product(s), reagents/conditions, starting material and/or name of the reaction as shown in the example.

5.1 #2

Determine how many chirality centers are in each of the following compounds.

3.15

1,3-butadiene reacts with HBr to form two different addition products. Draw the structure of the two products below.1.16 Complete the following table, filling in the missing major product(s), reagents/conditions, and/or starting material.

5.4 #1

Determine the relationship (identical, constitutional isomers, diastereomers, or enantiomers) between each pair of compounds shown below.

5.4 #2

Determine the relationship (identical, constitutional isomers, diastereomers, or enantiomers) between each pair of compounds shown below.

5.4 #4

Determine the relationship (identical, constitutional isomers, diastereomers, or enantiomers) between each pair of compounds shown below.

3.7 #2

Determine the structure of the alkene that could be used to prepare each of the alkyl halides shown below by addition of HCl. In cases where more than one alkene is possible, draw each.

9.14 #3

Draw a mechanism for each reaction shown below.

6.9

Draw a mechanism for the following reaction.

2.11

Draw all possible staggered and eclipsed conformations of 1-bromo-2-chloroethane sighting down the bond between carbon-1 and carbon-2. Rank the conformations in order of decreasing stability.

2.15

Draw all possible staggered and eclipsed conformations of 1-bromo-2-chloroethane sighting down the bond between carbon-1 and carbon-2. Rank the conformations in order of decreasing stability.

8.1 #1

Draw structures corresponding to the following IUPAC name:

7.1 d

Draw structures for the following compounds.

7.1 e

Draw structures for the following compounds.

2.3 c

Draw the correct structure for each of the following compounds: 1,1-diiodocyclobutane

5.2 #2

Draw the enantiomer, for each of the following compounds.

6.4 #1

Draw the product that you expect for each of the following SN2 reactions:

6.4 #2

Draw the product that you expect for each of the following SN2 reactions:

6.4 #4

Draw the product that you expect for each of the following SN2 reactions:

6.3 #6

Draw the products that you expect for each of the following SN1 reactions:

6.3 #8

Draw the products that you expect for each of the following SN1 reactions:

3.1 f

Draw the structure for each of the following compounds:

4.1 b

Draw the structure for the following compounds.

9.9 (enolates) #3

Draw the structure of all possible enolates for the carbonyl compounds shown below. Include both resonance forms for each enolate that you draw.

7.3 #3

Draw the structure of the alcohols that could be used to make the following alkenes using an elimination reaction.

3.10 #3

Draw the structure of the major product expected in the following hydration reactions.

3.14 #3

Draw the structures of the products expected in the following dihydroxylation and epoxidation reactions.

3.14 #4

Draw the structures of the products expected in the following dihydroxylation and epoxidation reactions.

3.12 #3

Draw the structures of the products expected in the following halogenation reactions.

3.13 #2

Draw the structures of the products expected in the following hydrogenation reactions.

3.13 #6

Draw the structures of the products expected in the following hydrogenation reactions.

3.13 #8

Draw the structures of the products expected in the following hydrogenation reactions.

3.11 #3

Draw the structures of the products expected in the following ozonolysis reactions.

9.13 a

For each of the aldol condensation products shown below draw a retrosynthesis showing: (i) the alpha and beta positions on the starting material (ii) the b-hydroxy carbonyl precursor (iii) the donor and acceptor starting materials

9.13 c

For each of the aldol condensation products shown below draw a retrosynthesis showing: (i) the alpha and beta positions on the starting material (ii) the b-hydroxy carbonyl precursor (iii) the donor and acceptor starting materials

9.13 d

For each of the aldol condensation products shown below draw a retrosynthesis showing: (i) the alpha and beta positions on the starting material (ii) the b-hydroxy carbonyl precursor (iii) the donor and acceptor starting materials

1.14 b

For each of the following acid/base reactions:(i) label the acid and conjugate acid (ii) write the approximate pKa under each (iii) predict the side that will be favored at equilibrium.

3.4 c

For each of the following alkenes, draw all possible intermediate carbocations that could result from the addition of a proton (H+) to the double bond and circle the carbocation that is expected to be more stable. If both carbocations have the same expected stability, state "same stability.

3.4 f

For each of the following alkenes, draw all possible intermediate carbocations that could result from the addition of a proton (H+) to the double bond and circle the carbocation that is expected to be more stable. If both carbocations have the same expected stability, state "same stability.

3.2 #1

For each of the following compounds determine if the double bond is in a cis or trans configuration, or neither cis nor trans.

3.2 #3

For each of the following compounds determine if the double bond is in a cis or trans configuration, or neither cis nor trans.

3.2 #4

For each of the following compounds determine if the double bond is in a cis or trans configuration, or neither cis nor trans.

3.2 #5

For each of the following compounds determine if the double bond is in a cis or trans configuration, or neither cis nor trans.

6.6 #1

For each of the following elimination reactions below, there are two hypothetical alkene products. In each case, (i) draw both products and (ii) circle the expected major product.

6.6 #3

For each of the following elimination reactions below, there are two hypothetical alkene products. In each case, (i) draw both products and (ii) circle the expected major product.

1.10 #4

For each of the following reactive carbon species, determine the formal charge on carbon.

3.6 #2

For each of the hydrohalogenation reactions below, draw the two possible products in the spaces provided. Draw the expected major regioisomer in space labelled "major product."

1.9 #2

For each structure below, label all missing formal charges.

5.3 #7

Identify the configuration of each chirality center in the following compounds.

4.3 #3 2nd part

Identify the reagents necessary to accomplish each of the following transformations.

5.5 #10

Identify whether each of the following compounds is chiral or achiral.

5.5 #2

Identify whether each of the following compounds is chiral or achiral.

5.5 #6

Identify whether each of the following compounds is chiral or achiral.

5.5 #8

Identify whether each of the following compounds is chiral or achiral.

4.7 b

In each box, provide the electron flow arrow(s) that describe the bond making and bond breaking occurring for each step or resonance form in the mechanism below.

7.2 #2

Predict the products you would expect from the following reactions. Indicate the major product in each case.

9.8 #2

Reactions Practice. Complete the following table, filling in the missing major product(s), reagents/conditions, starting material and/or reaction type.

9.8 #5

Reactions Practice. Complete the following table, filling in the missing major product(s), reagents/conditions, starting material and/or reaction type.

9.8 #6

Reactions Practice. Complete the following table, filling in the missing major product(s), reagents/conditions, starting material and/or reaction type.

7.4

Show how you could convert cyclohexanol into cyclohexane. More than one step may be necessary.

8.5 #2 (SN1)

Show how you could prepare tert-butyl propyl ether using a S N 1 method.

3.9 #3

Show the arrow-pushing mechanism for the following reactions.

4.6 a

Starting from benzene, devise a synthesis for the following compounds.