Salt Lake Community College/Department of Chemistry/Valcarce
Organic Chemistry 2318 Practice Test I (Chapter 2: Alkanes)
1. The chemical shown below is Sertraline, marketed by Pfizer under the trade name Zoloft. It is typical of the type of organic structures we will encounter in this course. Zoloft is prescribed as an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. Zoloft is primarily prescribed for major depressive disorder in adult outpatients as well as obsessivecompulsive, panic, and social anxiety disorders in both adults and children. In 2014, it was the third-most prescribed antidepressant on the U.S. retail market, with 37,208,000 prescriptions. Answer the following questions relating to the chemical structure of Zoloft.
What is the classification of this carbon?
CH3 NH
What is the classification of this carbon?
What is the hybridization state of this atom?
What is this bond type? Cl What is the hybridization state of this atom?
Cl What is this bond type?
What is the hybridization state of this atom?
2. Give the IUPAC name for the following compound:
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Salt Lake Community College/Department of Chemistry/Valcarce
3.
For this nomenclature question, please refer to the structure of the hydrocarbon shown below.
What is the IUPAC name of this substituent?
CH2 CH
What is the root name for this alkane?
CH2
CH2 CH2 CH2 CH2 CH2 CH2 CH3 CH2 NO 2 What is the IUPAC name of this substituent?
What is the IUPAC name of this substituent?
What is the IUPAC name of this substituent? What is the IUPAC name of this substituent?
4. Draw the chemical structural for the alkane named 2-vinyl-5-isobutyldodeacane.
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Salt Lake Community College/Department of Chemistry/Valcarce
Multiple Choice :
Answer the following multiple choice questions. Read each question carefully!
1. Identify the relationship between the following chemical structures? CH3 H3C
CH CH2 CH2 C CH2 CH2 CH3
&
CH3
___A.
Identical compounds.
___B.
Constitutional isomers
___C.
Different compounds with different chemical formulas.
___D.
None of the above.
2. Which of the following chemical structures is NOT 7,10-diethyl-6-isopropyl-2-methyltridecane. H3C
CH3
CH3
H3C
___A.
H3C
CH3
H3C
H3C
CH3
CH3 CH3 H3C
CH3
___B.
___C.
CH3
___D. CH3 CH2
CH2CH3
H3C CH CH2 CH2 CH2 CH CH CH2 CH2 CH CH2 CH3
CH3 CH
CH3 CH2
CH3
___E.
___F .
3. What is the classification of the alkyl group marked by the dashed line in the following alkane? CH3 CH2 CH2 CH2 CH2 CH2 CH2 CH CH2 CH2 CH2 CH2 CH2 CH2 CH3 CH3 C
CH2 CH2 CH3
CH3
___A. unsubstituted (0°)
___B. Primary (1°)
___D. Tertiary (3°)
___E. none of the above page 3
___C. Secondary (2°)
Salt Lake Community College/Department of Chemistry/Valcarce
4.
5.
Considering only the structural isomers shown that have the molecular formula C7H16, which isomer would have the most methylene carbons? ___A. 2,2-dimethylpentane
___B. 2,3-dimethylpentane
___C. 2,4-dimethylpentane
___D. 3-ethylpentane
___E. 3,3-dimethylpentane
___F. 2,2,3-trimethylbutane
Considering only the structural isomers shown that have the molecular formula C7H16, which isomer would give the lowest heat of combustion? ___A. 2,2-dimethylpentane
___B. 2,3-dimethylpentane
___C. 2,4-dimethylpentane
___D. 3-ethylpentane
___E. 3,3-dimethylpentane
___F. 2,2,3-trimethylbutane
6. Which of the following alkanes has a tert-butyl substituent? CH3 CH CH2 CH3
___A.
CH2 CH2 CH2 CH2 CH3
___B.
CH2 CH2 CH2 CH2 CH3
CH3
CH3
CH2 CH CH3
CH2 C
CH3
CH3
___C.
CH2 CH2 CH2 CH2 CH3
___D.
CH3
CH2 CH2 CH2 CH2 CH3
CH2 CH2 CH2 CH3
C CH3 CH3
___E. 7.
CH2 CH2 CH2 CH2 CH3
CH CH2CH3
___F.
CH3
The correct IUPAC name for the following compound is: ___A. 1-ethyl-3,3-dimethylcycloheptane
CH3
___B. 3-ethyl-1,1-dimethylcycloheptane
CH3
___C. 1-ethyl-3,3-dimethylcyclooctane ___D. 3-ethyl-1,1-dimethylcyclooctane ___E. 1,1-dimethyl-3-propylcycloheptane
CH2CH2CH3
___F. 1-propyl-3,3-dimethylcycloheptane
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Salt Lake Community College/Department of Chemistry/Valcarce
8.
When one mole of hydrocarbon A undergoes combustion with excess oxygen, combustion products are formed in the following proportions: 1 mol hydrocarbon A
7CO2(g) +
7H2O(g)
Hydrocarbon A has 5 methylene carbons, 1 methine carbons and 1 methyl carbon in its construction? Which of the following could be hydrocarbon A? ___A. heptane
___B. 1-ethylcyclopentane
___C. 1-ethylcyclohexane
___D. 1-ethyl-2-methylcyclobutane
___E. 3-methylhexane
___F. 2,2-dimethylpentane
___G. 1-propylcyclopentane 9. What is the IUPAC name for the neopentyl alkyl substituent? ___A. 1-methylbutyl
___B. 1,1-dimethylpropyl
___D. 2-methylpentyl
___E. 1,1-dimethylethyl
___C. 2,2-dimethylpropyl
10. The chemical shown below is Pethidine, more commonly referred to as Demerol. Demerol is a fast acting opiate analgesic drug that is used for the medical treatment of moderate to severe pain. O N
CH3
CH3CH2 O
How many sp2 hybridized atoms are found in Demerol? ___A. one
___B. two
___C. four
___D. five
___E. six
___F. seven
___G. eight
___H. ten
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