ACS ORGANIC CHEMISTRY FINAL EXAM
1. Which is the stronger acid, HCl or HBr? Explain briefly.
HCl is the stronger acid because Cl is more electronegative than Br.
HCl is the stronger acid because Cl is smaller than Br.
HBr is the stronger acid because Br is less electronegative than Cl.
HBr is the stronger acid because Br is larger than Cl.: HBr is the stronger acidbecause Br is
larger than Cl.
2. Which of the indicated protons in the given compound is the most acidic?
Proton A
Proton B
Proton C
Proton D: Proton D
3. Which of the given compounds is more acidic? Briefly explain.
X is the stronger acid because the acidic proton is on a more electronegativeatom.
X is the stronger acid because its conjugate base is stabilized by inductiveeffects.
Y is the stronger acid because its conjugate base is stabilized by resonance.
Y is the stronger acid because the acidic proton is stabilized by inductive effects.: Y is the
stronger acid because its conjugate base is stabilized by resonance.
4. Of the following, which is the strongest base?: A
5. All of the following are representations of cis-1,2-dimethylcyclohexane,EXCEPT:: D
6. All of the following are representations of 2-methylpentane, EXCEPT:: B
7. Which of the following is expected to have the largest heat of combustion?-
:C
8. Which of the following is a constitutional isomer of heptane?: D
9. Provide a systematic name for the following compound.
4-isopropylpentane
2-isopropylpentane
5,6-dimethylhexane
2,3-dimethylhexane: 2,3-dimethylhexane
, 10. Which of the following represents the most stable conformation ofcis-1,4-
dimethylcyclohexane?: C
11. Which of the following conformers has one or more gauche interactions?-
:B
12. Which of the following represents the most stable conformation of thegiven compound?:
C
13. Which of the following is the correct IUPAC name for the tertbutyl sub-stituent?
(1,1-dimethylethyl)(1,1,1-trimethyl)
(1-methyl-2-propyl)
2-methyl-2-propyl): (1,1-dimethylethyl)
14. What is the configuration of the chiral center in the following compound?R
SZ
Depends on T: R
15. What is the relationship between the following two compounds?Enantiomers
Diastereomers Constitutional isomers
Resonance forms: Diastereomers
16. Which of these compounds is expected to be optically active at roomtemperature?: D
17. Identify the meso compound(s).I only
II only
I and III only
I, II, and III: II only
18. Is the following compound chiral, and does it have an enantiomer?It is not chiral, and it
does not have an enantiomer.
It is not chiral, but it does have an enantiomer.It is chiral, and it has an enantiomer.
It is chiral, but it does not have an enantiomer.: It is not chiral, and it does nothave an
enantiomer.
19. Which is the correct hybridization state and geometry for the carbon atomin HCN?
sp, linear
sp2, trigonal planarsp3, tetrahedral
None of the above: sp, linear
20. The following structure has been drawn without formal charges. Whichstatement
1. Which is the stronger acid, HCl or HBr? Explain briefly.
HCl is the stronger acid because Cl is more electronegative than Br.
HCl is the stronger acid because Cl is smaller than Br.
HBr is the stronger acid because Br is less electronegative than Cl.
HBr is the stronger acid because Br is larger than Cl.: HBr is the stronger acidbecause Br is
larger than Cl.
2. Which of the indicated protons in the given compound is the most acidic?
Proton A
Proton B
Proton C
Proton D: Proton D
3. Which of the given compounds is more acidic? Briefly explain.
X is the stronger acid because the acidic proton is on a more electronegativeatom.
X is the stronger acid because its conjugate base is stabilized by inductiveeffects.
Y is the stronger acid because its conjugate base is stabilized by resonance.
Y is the stronger acid because the acidic proton is stabilized by inductive effects.: Y is the
stronger acid because its conjugate base is stabilized by resonance.
4. Of the following, which is the strongest base?: A
5. All of the following are representations of cis-1,2-dimethylcyclohexane,EXCEPT:: D
6. All of the following are representations of 2-methylpentane, EXCEPT:: B
7. Which of the following is expected to have the largest heat of combustion?-
:C
8. Which of the following is a constitutional isomer of heptane?: D
9. Provide a systematic name for the following compound.
4-isopropylpentane
2-isopropylpentane
5,6-dimethylhexane
2,3-dimethylhexane: 2,3-dimethylhexane
, 10. Which of the following represents the most stable conformation ofcis-1,4-
dimethylcyclohexane?: C
11. Which of the following conformers has one or more gauche interactions?-
:B
12. Which of the following represents the most stable conformation of thegiven compound?:
C
13. Which of the following is the correct IUPAC name for the tertbutyl sub-stituent?
(1,1-dimethylethyl)(1,1,1-trimethyl)
(1-methyl-2-propyl)
2-methyl-2-propyl): (1,1-dimethylethyl)
14. What is the configuration of the chiral center in the following compound?R
SZ
Depends on T: R
15. What is the relationship between the following two compounds?Enantiomers
Diastereomers Constitutional isomers
Resonance forms: Diastereomers
16. Which of these compounds is expected to be optically active at roomtemperature?: D
17. Identify the meso compound(s).I only
II only
I and III only
I, II, and III: II only
18. Is the following compound chiral, and does it have an enantiomer?It is not chiral, and it
does not have an enantiomer.
It is not chiral, but it does have an enantiomer.It is chiral, and it has an enantiomer.
It is chiral, but it does not have an enantiomer.: It is not chiral, and it does nothave an
enantiomer.
19. Which is the correct hybridization state and geometry for the carbon atomin HCN?
sp, linear
sp2, trigonal planarsp3, tetrahedral
None of the above: sp, linear
20. The following structure has been drawn without formal charges. Whichstatement
