Chapter 3 - Organic Compounds: Alkanes and Their Stereochemistry
MATCH a structure below to each of the following descriptions and place the letter corresponding to the structure in the blank.
O CH3 O O CH3
A.H B.CH3CHCH C. D. H NH2 Cl H3C CH3
O Cl CH3
E. F. CH3CHCH3 G. H
H
CH3
1. is an amino aldehyde.
Answer: B
2. is an aromatic ketone.
Answer: E
3. is a tertiary chloride.
Answer: C
4. is a cyclic alkane with two cis methyl groups.
Answer: C
5. Circle and name each functional group in the following structure.
O O O O OH
H
O cortisone acetate (active ingredient in steriod skin cream)
12 Chapter 3: Organic Compounds: Alkanes and Their Stereochemistry
Answer: O
ketone O ester O
ketone O OH alcohol
H ketone O alkene
Label the indicated atoms in the structure below as 1°, 2°, 3°, or 4°. O
7. O O HO OH 6. 9.
H 8. O
6. This atom is . Answer: 4°
7. This atom is . Answer: 2°
8. This atom is . Answer: 3°
9. This atom is . Answer: 1°
Label the following pairs of compounds as:
a. identical b. constitutional isomers c. neither
Place the letter of the correct answer in the blank below the structures. O
10. H and
O
Answer: b
Test Items for McMurry’s Organic Chemistry, Seventh Edition 13 11. CH3 CH2CH3
and
H3C CH3
Answer: c
CH3 12. and CH3
Answer: a
Provide proper IUPAC names for each compound below.
13. (CH3)2CHCH2CH2CH(CH2CH3)CH2C(CH3)3
Answer: 4-ethyl-2,2,7-trimethyloctane
14. Br CH3
H3CCHCH2CCH2CHCH2CH3
CH3 C(CH3)3
Answer: 7-bromo-3-ethyl-2,2,5,5-tetramethyloctane or 2-bromo-6-tert-butyl-4,4-dimethyloctane
CH2CH2CH3
15. CH3CHCH2CHCHCH3
CH2CH3 CH3
Answer: 5-isopropyl-3-methyloctane
14 Chapter 3: Organic Compounds: Alkanes and Their Stereochemistry
Consider the representation below to answer the following questions.
Z.
16. Provide the IUPAC name for compound Z.
Answer: 5-ethyl-3,4-dimethyloctane
Draw structures corresponding to each of the following names.
17. 4-isopropyl-6-ethyldecane
Answer:
18. 2-fluoro-3-methylpentane
Answer:
F
19. 4-(2,2-dibromoethyl)-3,5-dichloroheptane
Br
Br Answer:
Cl Cl
Test Items for McMurry’s Organic Chemistry, Seventh Edition 15 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. Draw a Newman projection of the anti conformation of 1,2-dichloroethane.
Answer: Cl H H
H H Cl
21. Draw a Newman projection of the gauche conformation of 1,2-dichloroethane.
Answer: Cl H Cl
H H
H
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.
O O F COH
N N Cipro N H
22. Circle the functional groups in the Cipro representation above.
Answer: O O F COH
N N N H
16 Chapter 3: Organic Compounds: Alkanes and Their Stereochemistry
Predict the hybridization of the indicated atoms in Cipro. 24. O O 23. F COH
N N 25. N H
23. The hybridization of this nitrogen atom is ______.
Answer: sp3
24. The hybridization of this carbon atom is ______.
Answer: sp2
25. The hybridization of this carbon atom is ______.
Answer: sp3
26. Put a box around the most polar bond in Cipro based on electronegativity values. O O F COH
N N Cipro N H
Answer: O O F COH
N N N H
Test Items for McMurry’s Organic Chemistry, Seventh Edition 17