chapter 2--the nature of organic compounds: alkanes · chapter 2--the nature of organic compounds:...
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Chapter 2--The Nature of Organic Compounds: Alkanes
1. Narrative 2-1
MATCH a structure below to each of the following descriptions and place the letter corresponding to the
structure in the blank.
Refer to Narrative 2-1. __________ is an amino aldehyde.
Full file at https://fratstock.eu2. Narrative 2-1
MATCH a structure below to each of the following descriptions and place the letter corresponding to the
structure in the blank.
Refer to Narrative 2-1. __________ is an aromatic ketone.
Full file at https://fratstock.eu3. Narrative 2-1
MATCH a structure below to each of the following descriptions and place the letter corresponding to the
structure in the blank.
Refer to Narrative 2-1. __________ is a tertiary chloride.
Full file at https://fratstock.eu4. Narrative 2-1
MATCH a structure below to each of the following descriptions and place the letter corresponding to the
structure in the blank.
Refer to Narrative 2-1. __________ is a cyclic alkane with two cis methyl groups.
5. Circle and name each functional group in the following structure.
Full file at https://fratstock.eu6. Narrative 2-2
Label the indicated atoms in the structure below as 1º, 2º, 3º, or 4º.
This atom is __________.
7. Narrative 2-2
Label the indicated atoms in the structure below as 1º, 2º, 3º, or 4º.
This atom is __________.
Full file at https://fratstock.eu8. Narrative 2-2
Label the indicated atoms in the structure below as 1º, 2º, 3º, or 4º.
This atom is __________.
9. Narrative 2-2
Label the indicated atoms in the structure below as 1º, 2º, 3º, or 4º.
This atom is __________.
Full file at https://fratstock.eu10. Narrative 2-3
Convert the following structures into skeletal drawings.
Refer to Narrative 2-3.
11. Narrative 2-3
Convert the following structures into skeletal drawings.
Refer to Narrative 2-3.
Full file at https://fratstock.eu12. This skeletal structure corresponds to the molecular formula:
a. C5H6O6
b. C7H10O6
c. C6H6O6
d. C6H8O6
13. Narrative 2-4
The following questions refer to cocaine, whose skeletal structure is shown below.
Refer to Narrative 2-4. The number of hydrogens bonded to this carbon is _______.
Full file at https://fratstock.eu14. Narrative 2-4
The following questions refer to cocaine, whose skeletal structure is shown below.
Refer to Narrative 2-4. The number of hydrogens bonded to this carbon is _______.
15. Narrative 2-4
The following questions refer to cocaine, whose skeletal structure is shown below.
Refer to Narrative 2-4. The number of hydrogens bonded to this carbon is _______.
Full file at https://fratstock.eu16. Narrative 2-4
The following questions refer to cocaine, whose skeletal structure is shown below.
Refer to Narrative 2-4. The molecular formula for cocaine is _______.
17. Narrative 2-5
Label the following pairs of compounds as:
a. identical
b. constitutional isomers
c. stereoisomers
Place the letter of the correct answer in the blank to the left of the structures.
Refer to Narrative 2-5. _____
Full file at https://fratstock.eu18. Narrative 2-5
Label the following pairs of compounds as:
a. identical
b. constitutional isomers
c. stereoisomers
Place the letter of the correct answer in the blank to the left of the structures.
Refer to Narrative 2-5. _____
19. Narrative 2-5
Label the following pairs of compounds as:
a. identical
b. constitutional isomers
c. stereoisomers
Place the letter of the correct answer in the blank to the left of the structures.
Refer to Narrative 2-5. _____
Full file at https://fratstock.eu20. Provide the proper IUPAC name for the compound below.
(CH3)2CHCH2CH2CH(CH2CH3)CH2C(CH3)3
21. Provide the proper IUPAC name for the compound below.
22. Provide the proper IUPAC name for the compound below.
Full file at https://fratstock.eu23. Narrative 2-6
Consider the representation below to answer the following questions.
Refer to Narrative 2-6. Provide the IUPAC name for compound Z.
24. Narrative 2-6
Consider the representation below to answer the following questions.
Refer to Narrative 2-6. Draw a constitutional isomer of compound Z. that contains an isopropyl group.
Full file at https://fratstock.eu25. Draw a structure corresponding to the following name:
cis-1-sec-butyl-2-ethylcyclopentane
26. Draw a structure corresponding to the following name:
3-cyclobutylpentane
27. There are seven (7) constitutional isomers for cycloalkane formula C6H12. Draw them.
28. Draw the two stereoisomers of 1,3-dibromocyclobutane.
Full file at https://fratstock.eu29. Narrative 2-7
Consider the conformations of 2-methylbutane shown below to answer the following questions.
Refer to Narrative 2-7. Which of the structures represents the most stable conformation of 2-methylbutane?
30. Narrative 2-7
Consider the conformations of 2-methylbutane shown below to answer the following questions.
Refer to Narrative 2-7. Which of the structures represents the least stable conformation of 2-methylbutane?
Full file at https://fratstock.eu31. Draw the Newman projection for the specified conformations for rotation about the C-C bond of
1,2-dichloroethane.
There are two staggered conformations of 1,2-dichloroethane. Draw them.
32. Draw the Newman projection for the specified conformations for rotation about the C-C bond of
1,2-dichloroethane.
There are two eclipsed conformations of 1,2-dichloroethane. Draw them.
33. Narrative 2-8
Refer to the structure below to answer the following questions:
Refer to Narrative 2-8. Which of the labeled bonds in the structure are equatorial bonds?
Full file at https://fratstock.eu34. Narrative 2-8
Refer to the structure below to answer the following questions:
Refer to Narrative 2-8. Which of the labeled bonds is trans to bond b?
35. Narrative 2-8
Refer to the structure below to answer the following questions:
Refer to Narrative 2-8. Which bonds have a 1,3-diaxial interaction with each other?
Full file at https://fratstock.eu36. Narrative 2-9
For each substituted cyclohexane below, draw its ring-flip isomer. Circle the most stable conformation.
Refer to Narrative 2-9.
37. Narrative 2-9
For each substituted cyclohexane below, draw its ring-flip isomer. Circle the most stable conformation.
Refer to Narrative 2-9.
Full file at https://fratstock.eu38. Narrative 2-9
For each substituted cyclohexane below, draw its ring-flip isomer. Circle the most stable conformation.
Refer to Narrative 2-9.
39. Narrative 2-10
Label each pair of compounds below as:
a. conformational isomers
b. stereoisomers
c. constitutional isomers
d. identical
Refer to Narrative 2-10.
Full file at https://fratstock.eu40. Narrative 2-10
Label each pair of compounds below as:
a. conformational isomers
b. stereoisomers
c. constitutional isomers
d. identical
Refer to Narrative 2-10.
Full file at https://fratstock.eu41. Narrative 2-10
Label each pair of compounds below as:
a. conformational isomers
b. stereoisomers
c. constitutional isomers
d. identical
Refer to Narrative 2-10.
Full file at https://fratstock.eu42. Narrative 2-10
Label each pair of compounds below as:
a. conformational isomers
b. stereoisomers
c. constitutional isomers
d. identical
Refer to Narrative 2-10.
Full file at https://fratstock.eu
Chapter 2--The Nature of Organic Compounds: Alkanes Key
1. Narrative 2-1
MATCH a structure below to each of the following descriptions and place the letter corresponding to the
structure in the blank.
Refer to Narrative 2-1. __________ is an amino aldehyde.
B
Full file at https://fratstock.eu2. Narrative 2-1
MATCH a structure below to each of the following descriptions and place the letter corresponding to the
structure in the blank.
Refer to Narrative 2-1. __________ is an aromatic ketone.
E
3. Narrative 2-1
MATCH a structure below to each of the following descriptions and place the letter corresponding to the
structure in the blank.
Refer to Narrative 2-1. __________ is a tertiary chloride.
C
Full file at https://fratstock.eu4. Narrative 2-1
MATCH a structure below to each of the following descriptions and place the letter corresponding to the
structure in the blank.
Refer to Narrative 2-1. __________ is a cyclic alkane with two cis methyl groups.
C
5. Circle and name each functional group in the following structure.
Full file at https://fratstock.eu6. Narrative 2-2
Label the indicated atoms in the structure below as 1º, 2º, 3º, or 4º.
This atom is __________.
4º
7. Narrative 2-2
Label the indicated atoms in the structure below as 1º, 2º, 3º, or 4º.
This atom is __________.
2º
Full file at https://fratstock.eu8. Narrative 2-2
Label the indicated atoms in the structure below as 1º, 2º, 3º, or 4º.
This atom is __________.
3º
9. Narrative 2-2
Label the indicated atoms in the structure below as 1º, 2º, 3º, or 4º.
This atom is __________.
1º
Full file at https://fratstock.eu10. Narrative 2-3
Convert the following structures into skeletal drawings.
Refer to Narrative 2-3.
11. Narrative 2-3
Convert the following structures into skeletal drawings.
Refer to Narrative 2-3.
Full file at https://fratstock.eu12. This skeletal structure corresponds to the molecular formula:
a. C5H6O6
b. C7H10O6
c. C6H6O6
d. C6H8O6
d
13. Narrative 2-4
The following questions refer to cocaine, whose skeletal structure is shown below.
Refer to Narrative 2-4. The number of hydrogens bonded to this carbon is _______.
two
Full file at https://fratstock.eu14. Narrative 2-4
The following questions refer to cocaine, whose skeletal structure is shown below.
Refer to Narrative 2-4. The number of hydrogens bonded to this carbon is _______.
one
15. Narrative 2-4
The following questions refer to cocaine, whose skeletal structure is shown below.
Refer to Narrative 2-4. The number of hydrogens bonded to this carbon is _______.
zero
Full file at https://fratstock.eu16. Narrative 2-4
The following questions refer to cocaine, whose skeletal structure is shown below.
Refer to Narrative 2-4. The molecular formula for cocaine is _______.
C17H21NO4
17. Narrative 2-5
Label the following pairs of compounds as:
a. identical
b. constitutional isomers
c. stereoisomers
Place the letter of the correct answer in the blank to the left of the structures.
Refer to Narrative 2-5. _____
b
Full file at https://fratstock.eu18. Narrative 2-5
Label the following pairs of compounds as:
a. identical
b. constitutional isomers
c. stereoisomers
Place the letter of the correct answer in the blank to the left of the structures.
Refer to Narrative 2-5. _____
c
19. Narrative 2-5
Label the following pairs of compounds as:
a. identical
b. constitutional isomers
c. stereoisomers
Place the letter of the correct answer in the blank to the left of the structures.
Refer to Narrative 2-5. _____
a
20. Provide the proper IUPAC name for the compound below.
(CH3)2CHCH2CH2CH(CH2CH3)CH2C(CH3)3
4-ethyl-2,2,7-trimethyloctane
Full file at https://fratstock.eu21. Provide the proper IUPAC name for the compound below.
trans-1-tert-butyl-4-ethylcyclohexane or trans-1-(1,1-dimethylethyl)-4-ethylcyclohexane
22. Provide the proper IUPAC name for the compound below.
3-methyl-5-isopropyloctane or 3-methyl-5-(1-methylethyl)octane
23. Narrative 2-6
Consider the representation below to answer the following questions.
Refer to Narrative 2-6. Provide the IUPAC name for compound Z.
5-ethyl-3,4-dimethyloctane
Full file at https://fratstock.eu24. Narrative 2-6
Consider the representation below to answer the following questions.
Refer to Narrative 2-6. Draw a constitutional isomer of compound Z. that contains an isopropyl group.
25. Draw a structure corresponding to the following name:
cis-1-sec-butyl-2-ethylcyclopentane
26. Draw a structure corresponding to the following name:
3-cyclobutylpentane
Full file at https://fratstock.eu27. There are seven (7) constitutional isomers for cycloalkane formula C6H12. Draw them.
28. Draw the two stereoisomers of 1,3-dibromocyclobutane.
29. Narrative 2-7
Consider the conformations of 2-methylbutane shown below to answer the following questions.
Refer to Narrative 2-7. Which of the structures represents the most stable conformation of 2-methylbutane?
A
Full file at https://fratstock.eu30. Narrative 2-7
Consider the conformations of 2-methylbutane shown below to answer the following questions.
Refer to Narrative 2-7. Which of the structures represents the least stable conformation of 2-methylbutane?
B
31. Draw the Newman projection for the specified conformations for rotation about the C-C bond of
1,2-dichloroethane.
There are two staggered conformations of 1,2-dichloroethane. Draw them.
32. Draw the Newman projection for the specified conformations for rotation about the C-C bond of
1,2-dichloroethane.
There are two eclipsed conformations of 1,2-dichloroethane. Draw them.
Full file at https://fratstock.eu33. Narrative 2-8
Refer to the structure below to answer the following questions:
Refer to Narrative 2-8. Which of the labeled bonds in the structure are equatorial bonds?
a and d
34. Narrative 2-8
Refer to the structure below to answer the following questions:
Refer to Narrative 2-8. Which of the labeled bonds is trans to bond b?
e
35. Narrative 2-8
Refer to the structure below to answer the following questions:
Refer to Narrative 2-8. Which bonds have a 1,3-diaxial interaction with each other?
b and c
Full file at https://fratstock.eu36. Narrative 2-9
For each substituted cyclohexane below, draw its ring-flip isomer. Circle the most stable conformation.
Refer to Narrative 2-9.
37. Narrative 2-9
For each substituted cyclohexane below, draw its ring-flip isomer. Circle the most stable conformation.
Refer to Narrative 2-9.
Full file at https://fratstock.eu38. Narrative 2-9
For each substituted cyclohexane below, draw its ring-flip isomer. Circle the most stable conformation.
Refer to Narrative 2-9.
39. Narrative 2-10
Label each pair of compounds below as:
a. conformational isomers
b. stereoisomers
c. constitutional isomers
d. identical
Refer to Narrative 2-10.
b
Full file at https://fratstock.eu40. Narrative 2-10
Label each pair of compounds below as:
a. conformational isomers
b. stereoisomers
c. constitutional isomers
d. identical
Refer to Narrative 2-10.
c
41. Narrative 2-10
Label each pair of compounds below as:
a. conformational isomers
b. stereoisomers
c. constitutional isomers
d. identical
Refer to Narrative 2-10.
d
Full file at https://fratstock.eu42. Narrative 2-10
Label each pair of compounds below as:
a. conformational isomers
b. stereoisomers
c. constitutional isomers
d. identical
Refer to Narrative 2-10.
a