Organic Chemistry: Concepts and Applications - Headley Allan D. 2020

Heteroatomic Functional Groups and Organic Nomenclature
End of Chapter Problems

1. 3.30 Give the structure of a molecule that has each of the following functional groups.

a) alcohol

b) carboxylic acid

c) alkyne

d) alkene

e) amine

2. 3.31 Determine if the names given below for each of the molecules given are correct. If not, give the correct IUPAC name.Image

3. 3.32 Give the name of the functional group found in each of the following molecules.Image

4. 3.33 Give line-angle formulas for the following molecules.

i) Ethyl ethanoate

vi) Methyl-2-hexanethiol

ii) 2-Chlorohexanal

vii) 4-Methyl-2-pentanamine

iii) 6-Methyl-4-hepten-2-one

viii) 4-Bromo-3-methyl-2-pentanone

iv) 3-Chlorobutanoic acid

ix) 3-Bromobutanal

v) 3-Hexanol


5. 3.34 There are four different alcohols with the molecular formula C4H10O. Give the line-angle formula for each and indicate which are primary, secondary, or tertiary.

6. 3.35 Give IUPAC names for the following molecules.Image

7. 3.36 Shown below is the structure of ethambutol, which is used to treat tuberculosis. Identify the functional groups present in ethambutol.Image

8. 3.37 Shown below is the lipid-lowering drug, simvastatin. Identify the functional groups present in simvastatin.Image

9. 3.38 Naltrexone is used to treat narcotic addition, identify all the functional groups present in naltrexone.Image

10. 3.39 The drug acebutolol is used in the treatment of various heart diseases. Identify the functional groups present in acebutolol.Image

11. 3.40 An unknown compound shows a strong IR band at 1710 cm−1 and has a molecular formula of C5H10O, it was shown to be an acyclic compound. What is a most likely structure of this unknown compound?

12. 3.41 For each of the following molecular formulas shown below, give a line-angle structure that contains only the indicated functionality.

a)C5H8O2 (carboxylic acid)

g)C3H9N (2o amine)

b)C6H10O (ketone)

h)C4H11N (3o amine)

c)C6H10 (alkyne)

i)C4H8O2 (ester)

d)C5H10O (aldehyde)

j)C5H10O2 (carboxylic acid)

e)C3H5N (nitrile)

k)C4H10O (alcohol)

f)C4H10O (ether)

l)C5H11NO (amide)

13. 3.42 Label each alcohol shown below as primary (1°), secondary (2°), or tertiary (3°).Image

14. 3.43 Give the structures of all alcohol isomers with the molecular formula C5H12O, name them and indicate which are primary, secondary, or tertiary.

15. 3.44 Give the IUPAC names for each of the following molecules.Image

16. 3.45 Give line-angle structures for the following compounds.

1. 1-Pentyn-3-ol

2. 3-Chloro-2-butenoic acid

3. 2-Chloro-3-methylbutanal

4. 2-Methyl-2-hexenal

5. 4-Methyl-2-pentanone

6. Ethyl ethanoate

7. 5-Methyl-3-hexen-2-one

8. Propyl butanoate

9. 2-Chlorohexanal

10. 3-Bromo-4-methylcyclohexanone

11. 6-Methyl-4-hepten-2-one

12. o) 3-Hydroxybutanal

13. 3-Hexanol

14. p) 3-Chloro-2-butenoic acid

15. 2-Chloro-2-hexenal

16. q)trans-2,3-Diethyloxirane

17. 3-Bromo-4-methylcyclopentanoner)

18. 3-Methylpentanenitrile

17. 3.46 Shown below are the structures of four compounds with different functional groups.Image

The IR spectra of the compounds given above are shown below. Utilizing the information contained in Table 3.1, match the spectra with the compounds given.

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Utilizing the information contained in Table 3.1, match the spectra with the compounds given.