Name: ________________________ Class: ___________________ Date: __________ ID: A

Orgo 1-Test 3

Short Answer

To answer the question(s) below consider the following reaction:

When cyclohexene reacts with chlorine in carbon tetrachloride the trans-dihalide is formed.

1. Write the complete stepwise mechanism for this reaction. Be sure to show all intermediate structures and all
electron flow using arrows.
2. Since the two chlorine atoms add to opposite faces of the cyclohexene double bond, we say that the reaction
occurs with:

a. syn stereochemistry
b. cis stereochemistry
c. anti stereochemistry
d. retention of stereochemistry
3. Provide the IUPAC name for the product of the reaction of cyclohexene with chlorine.
4. Draw both chair conformations of trans-1,2-dichlorocyclohexane on the templates provided below. Circle the
least stable conformation.

Consider the reaction below to answer the following question(s).

When dichlorocarbene is generated in the presence of an alkene, a dichlorocyclopropane is formed.

5. Write the complete stepwise mechanism for the formation of dichlorocarbene, CCl2. Show all intermediate
structures and show all electron flow with arrows.
6. Draw the complete Lewis electron dot structure for dichlorocarbene, CCl2.

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Name: ________________________ ID: A

7. In the reaction of an alkene with dichlorocarbene, the dichlorocarbene is the:

a. electrophile.
b. Lewis base.
c. nucleophile.
d. both b and c.
8. The reaction of an alkene with dichlorocarbene is:

a. regiospecific.
b. Markovnikov.
c. stereospecific.
d. non-Markovnikov.

Predict the products of each reaction below. Indicate regiochemistry and stereochemistry when relevant.

9.

10.

11.

12.

Draw structures corresponding to each of the given names.

13. 4-bromo-3,3-dimethyl-1-hexen-5-yne
14. acetylene

To answer the following question(s), consider the information below:

The heat of hydrogenation of 1,4-pentadiene is 254.4 kJ/mol. The heat of hydrogenation of 1-pentyne is
approximately 292.9 kJ/mol.

15. Which structure is more stable, 1,4-pentadiene or 1-pentyne?

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Name: ________________________ ID: A

Predict the product of each reaction below. Be sure to indicate stereochemistry when appropriate.

16.

Show all reagents and intermediates necessary to carry out the following conversions.

17.

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

18.

19.

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Name: ________________________ ID: A

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

20. The configuration of this carbon atom (A) is _____.

21. The configuration of this carbon atom (B) is _____.
22. The configuration of this carbon atom (C) is _____.
23. The configuration of this carbon atom (D) is _____.
24. The configuration of this carbon atom (E) is _____.

Label each pair of stereoisomers below as:

a. enantiomers
b. diastereomers
c. identical

Place the letter of the correct answer in the blank to the left of the pair of stereoisomers.

25. _____

26. _____

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Name: ________________________ ID: A

27. Estriol, a potent estrogenic hormone, has been isolated from the urine of pregnant women. When 40 mg of
estriol is dissolved in 1.0 mL of dioxane and placed in a sample tube with 1 dm path length a rotation of
+2.32° is observed. Calculate the specific rotation for estriol.

5
 ID: A

Orgo 1-Test 3
Answer Section

SHORT ANSWER

1. ANS:

PTS: 1
2. ANS:
c

PTS: 1
3. ANS:
trans-1,2-dichlorocyclohexane

PTS: 1
4. ANS:

PTS: 1
5. ANS:

PTS: 1
6. ANS:

PTS: 1
7. ANS:
a

PTS: 1

1
 ID: A

8. ANS:
c

PTS: 1
9. ANS:

PTS: 1
10. ANS:

PTS: 1
11. ANS:

PTS: 1
12. ANS:

PTS: 1
13. ANS:

PTS: 1
14. ANS:

PTS: 1
15. ANS:
1,4-pentadiene

PTS: 1

2
 ID: A

16. ANS:

PTS: 1
17. ANS:

PTS: 1
18. ANS:

PTS: 1
19. ANS:

PTS: 1
20. ANS:
R

PTS: 1

3
 ID: A

21. ANS:
S

PTS: 1
22. ANS:
R

PTS: 1
23. ANS:
S

PTS: 1
24. ANS:
S

PTS: 1
25. ANS:
b

PTS: 1
26. ANS:
c

PTS: 1
27. ANS:
+2.32°
[α ] D = = +58°
1 dm × 0.040 g/mL

PTS: 1