Pima County Community College

OCHEM 1

Chapter 3 Organic Compounds: Alkanes and Their Stereochemistry

SHORT ANSWER

Exhibit 3-1

MATCH a structure below to each of the following descriptions and place the letter corresponding to the structure in the blank.

1)          is an amino aldehyde.

2.     is an aromatic ketone.

3.     is a tertiary chloride.

4.     is a cyclic alkane with two cis methyl groups.

5. Circle and name each functional group in the following structure.

Exhibit 3-2

Label the indicated atoms in the structure below as 1?, 2?, 3?, or 4?.

6. Refer to Exhibit 3-2. The atom at A is                  .

7. Refer to Exhibit 3-2. The atom at B is                  .

8. Refer to Exhibit 3-2. The atom at C is                   .

9. Refer to Exhibit 3-2. The atom at D is                  .

Exhibit 3-3

Label the following pairs of compounds as:

identical constitutional isomers neither

Place the letter of the correct answer in the blank.

10.                 

11.                 

12.                 

IUPAC Naming Instructions: Provide proper IUPAC names.

13. Name: (CH₃)₂CHCH₂CH₂CH(CH₂CH₃)CH₂C(CH₃)₃

14. Name:

15. Name:

16. Name:

Drawing Instructions: Draw skeletal structures corresponding to each of the given names.

17. Draw: 6-ethyl-4-isopropyldecane

18. Draw: 2-fluoro-3-methylpentane

19. Draw: 4-(2,2-dibromoethyl)-3,5-dichloroheptane

Exhibit 3-4

Experiments have shown that for 1,2-dichloroethane, ClCH₂CH₂Cl, in carbon tetrachloride solution at 25

°C, 70% of the molecules are in the anti and 30% are in the gauche conformation.

20. Refer to Exhibit 3-4. Draw a Newman projection of the anti conformation of 1,2-dichloroethane.

21. Refer to Exhibit 3-4. Draw a Newman projection of the gauche conformation of 1,2-dichloroethane. Explain why the majority of the molecules are not in the gauche conformation.

Exhibit 3-5

Cipro? (Ciprofloxacin) is a synthetic broad spectrum antibacterial agent. It was most recently in the news as the antibiotic of choice for the treatment of anthrax. The structure of Cipro? is shown below.

22. Refer to Exhibit 3-5. Circle the functional groups in the Cipro? representation above.

Exhibit 3-6

Predict the hybridization of the indicated atoms in Cipro? .

23. Refer to Exhibit 3-6. The hybridization of this nitrogen atom (A) is                          .

24. Refer to Exhibit 3-6. The hybridization of this carbon atom (B) is                          .

25. Refer to Exhibit 3-6. The hybridization of this carbon atom (C) is                          .

26. Put a box around the most polar bond in Cipro? based on electronegativity values.

27. Name the following hydrocarbon.

28. How many eclipsed conformations can be drawn?

29. Draw the staggered conformations.

30. Arrange the following conformation from lowest to highest energy.

31. Explain your energy order from lowest to highest.

32. Draw at least four isomers with molecular formula given below.

C₄H₁₀O

MULTIPLE CHOICE

1. Which of the following functional groups if bonded to a three-carbon chain would have the largest

?– charge?

1. alcohol                                                                       
2. phosphate
3. ether                                                                          
4. sulfide

2. Which of the following functional groups contains a carbonyl group?

1. ketone
2. ester carboxylic acid amide
3. All contain a carbonyl group.

3. How many isomeric chloroalkanes have the molecular formula shown below?

C₄H₉Cl

A. 2                                                                                      B. 4

C. 3                                                                                       D. 5