CHEM 31 (Maam Anj) Chemical Nomenclature of Organic Compounds I. ALKANES A. Give the structural (skeletal) formula of: 1.

4-t-butylheptane 2. 6,6-dimethyl-5-(1,2,2-trimethylpropyl)dodecane 3. 3,4,5-trimethyl-4-propyloctane 4. 6-(3-methylbutyl)-undecane 5. 3,4,4,5-tetramethylheptane B. Give the systematic (IUPAC) name of: 1. (CH3)3CCH2C(CH3)3 2. (CH3)3CHCH2CH2CH(C2H5)2 3. (CH3)2CHCH(CH3)CH2C(C2H5)2CH3 4. (CH3CH2)4C

1. 2. 3. 4. 5.

2-dimethylpropane 3-propylhexane 3,5,6,7-tetramethylnonane 3-isopropyl-5,5-dimethyloctane 3,4,5-trimethyl-4-butyloctane

II. CYCLOALKANES A. Give the structural (skeletal) formula of: 1. ethylcyclopentane 2. cis-1,3-dimethylcyclobutane 3. cyclohexylcyclohexane 4. trans-2-chloro-1-isobutylcyclohexane 5. 1,1-dimethyl-4-chlorocycloheptane B. Give the systematic (IUPAC) name of:

1. 5. 2. 3. 6. 4. 7. 5.

8.

6. III. ALKYL HALIDES

9.

A. Draw the structures and provide systematic names for 1-3 by substituting a chlorine for a hydrogen of methylcyclohexane: 1. a primary alkyl halide 2. a tertiary alkyl halide

10. C. Find out why each of the following names is incorrect. Give the correct name:

3. three secondary alkyl halides

1 of 6

B. Name the following compounds, and tell whether each alkyl halide is primary, secondary, or tertiary: 1. 2. 3. 4.

5. 6.

7.

8.

5.

6. IV. ALKENES A. Give the structural (skeletal) formula of: 1. trans-3,4-dimethyl-2-pentene 2. (Z)-2-bromo-2-pentene 3. trans-3,4-dimethylcyclobutane 4. (E)-3-methyl-2-hexene 5. (Z)-3-chloro-4-methyl-3-hexene 6. 3-methylcyclohexene B. Give the IUPAC name of: 1. 2.

9.

10. C. Molly Kule was a lab technician who was asked by her supervisor to add names to the labels on a collection of alkenes that showed only structures on the labels. How many did Molly get right? Correct the incorrect names.

V. ALKYNES A. Give the structural (skeletal) formula of: 1. isopropylacetylene 2. dimethylacetylene

3.

3. cyclopropylacteylene 4. vinylacetylene

4.

5. 3-methyl-1-pentyne

2 of 6

6. 1-chloro-3-hexyne 7. propargyl chloride 8. cyclooctyne 9. dodec-4-ene-2-yne 10. 1,5-diiodopent-3-en-1-yne B. Give the IUPAC name of: 1. 2. 6. 5. 4. 3.

3.

7. VII. ETHERS AND EPOXIDES A. Draw the structural formula for: 1. Isobutyl methyl ether 2. methyl ethynyl ether

4.

5. VI. ALCOHOLS A. Draw the structural formula for: 1. neopentyl alcohol 2. ethane-1,2-diol 3. 2-ethyl-5-methylcyclohexanol 4. 6-bromo-4-ethyl-2-heptanol 5. 2-chloro-3-pentanol 6. benzyl alcohol 7. propane-1,2,3-triol 8. isoamyl alcohol B. Give each of the following compounds a systematic name, and indicate whether each is a primary, secondary, or tertiary alcohol: 1. 4. 2. 3 of 6

3. 4-t-butyl-3-methoxyheptane 4. diallyl ether 5. 3-isopropoxypenta-1,4-diyne 6. 2,2,3,3-tetramethyloxirane 7. 2,3-epoxy-2-methylpentane B. Give each of the following compounds a systematic name, and indicate whether each is a primary, secondary, or tertiary alcohol: 1. 2.

3.

IX. THIOLS (MERCAPTANS) AND SULFIDES (THIOETHERS) 5. A. Draw the structure of each of the following compounds: 1. ethyl neopentyl sulfide 2. 2-methylthiocyclopentanone 3. cyclohexanethiol 4. 2-methyl-2-propanethiol 5. 1,3-propenedithiol B. Give the systematic and/or common name of: 2. methyldipropylamine 3. N-ethylethanamine 2. 3. 1. (CH3CH2CH2)2S

6. VIII. AMINES A. Draw the structure of: 1. 2-methyl-N-propyl-1-propanamine

4. N,N-dimethylpentan-3-amine 5. 5-methylhexan-1-amine 6. Cyclohexylethylmethylamine B. For each of the following compounds, give the systematic name and the common name (for those that have common names), and indicate whether the amines are primary, secondary, tertiary or quaternary: 1.

4. 5. X. AROMATIC COMPOUNDS A. Draw the structure of: 1. m-divinylbenzene 2. o-diisopropylbenzene 3. 2,4-dinitrotoluene

2. 3.

4. 3-chlorotoluene 5. p-isobutylphenol

4.

6. m-chlorobenzonitrile 7. 2-bromo-4-iodophenol 8. o-nitroaniline

5.

9. phenylacetonitrile 10. ortho-chlorobenzenesulfonic acid B. Give the systematic name of:

6.

7.

1.

2. 4 of 6

1. -methoxyvaleric acid 2. p-toluic acid 3. 3. cyclopentanecarboxylic acid 4. propenoic acid 5. 2-hydroxypropane- 1,2,3-tricarboxylic acid 4. B. Give the systematic name of:

5. XI. ALDEHYDES AND KETONES A. Draw the structure and give the systematic name of: 1. acetone 2. methyl isobutyl ketone 3. formaldehyde 4. valeraldehyde 5. -bromopropionaldehyde 6. 2,4-pentanedione 7. 2-(3-oxopentyl)-cyclohexanone 8. Butyrophenone 9. 4-hexen-2-one 10. benzophenone B. Give the systematic name of:

1.

2. 3. 4.

5. XIII. CARBOXYLIC ACID DERIVATIVES A. Draw the structure of: 1. N,3-diethylhexanamide 2. cyclohexanecarboxamide 3. acetic formic anhydride 4. potassium methylbutyrate 5. N,N-dimethylformamide

1.

6. cyclohexanecarbonyl chloride 7. benzoic anhydride

2. 3.

8. 3-methylbutanenitrile 9. N-benzylethanamide 10. 2-azacyclobutanone B. Give the systematic name of:

4.

5. XII. CARBOXYLIC COMPOUNDS A. Draw the structure of:

1.

2. 5 of 6

3. 4.

VI

VII

5. VIII 6. 7. XI

8. 9. 10. XIV. Look at the structures of some organic compounds. Name the functional group present in each molecule and encircle the part of the molecule that you refer to. What is the IHD of each compound? Support your answer with calculations

II

III

IV

6 of 6

7 of 6