Deck 3: An Introduction to Organic Compounds

Question 1

Provide an acceptable name for the alkane shown below.

Answer 1

5-sec-butyl-2,2-dimethylnonane or
2,2-dimethyl-5-(1-methylpropyl)nonane

Question 2

Draw an acceptable structure for 4-t-butyloctane.

Answer 2

Question 3

Draw an acceptable structure for 3-ethyl-3-methylhexane.

Answer 3

Question 4

Give structures for the three isomers with molecular formula C₅H₁₂ and provide the common name of each.

Question 5

Draw an acceptable structure for 6-ethyl-2,6, 7-trimethyl-5-propylnonane.

Question 6

Draw an acceptable structure for 4-isopropyl-2-methylheptane.

Question 7

Give the IUPAC name for the following structure:

A)2-methyl-3-ethylheptane
B)3-ethyl-2-methylheptane
C)5-Isopropyloctane
D)4-Isopropyloctane
E)2-methyl-3-propylheptane

Question 8

Which of the following is a tertiary amine?

A)
B)
C)
D)
E)

Question 9

Provide an acceptable name for the alkane shown below.

Question 10

Provide an acceptable name for the alkane shown below.

Question 11

Provide an acceptable name for the alkane shown below.

Question 12

Provide an acceptable name for the alkane shown below.
CH₃CH₂CH₂CH₂CH₂CH₃

Question 13

There is something wrong with the following name. Write the structure and correct the name: 2-ethylpropane.

Question 14

Identify the number of tertiary carbons in the following structure.

A)2
B)3
C)4
D)5
E)6

Question 15

There are 8 isomers that have the molecular formula C₅H₁₁Br. How many of these are tertiary alkyl bromides?

A)0
B)1
C)2
D)3
E)8

Question 16

Provide an acceptable name for the alkane shown below.

Question 17

Provide an acceptable name for the alkane shown below.

Question 18

Provide an acceptable name for the alkane shown below.

Question 19

Which of the following is sec-butyl alcohol?

A)CH₃CH₂CH₂CH₂OH
B)CH₃CH(OH)CH₂CH₃
C)(CH₃)₂CHCH₂OH
D)(CH₃)₂CHOH
E)(CH₃)₂CHOCH₃

Question 20

What is the common name for the following structure?

A)Isobutane
B)Isopropylmethane
C)t-Butane
D)n-Butane
E)sec-Butane

Question 21

Provide an acceptable name for the compound shown below.

Question 22

Draw all possible constitutional isomers for C₂H₆O and give common names for each structure.

Question 23

Give the systematic name of the alkane shown below.

Question 24

Which of the following is diisopropyl ether?

A)CH₃CH₂CH₂-O-CH₂CH₂CH₃
B)
C)CH₃CH₂CH₂OCH(CH₃)₂
D)(CH₃)₃COC(CH₃)₃
E)(CH₃)₂CHOCH(CH₃)₂

Question 25

Name the compound.

A)2-cyclopentyl-4-methylhexane
B)5-cyclopentyl-3-methylhexane
C)1-cyclopentyl-1,3-dimethylpentane
D)2-cyclopentyl-4-methylheptane
E)5-cyclopentyl-3-methylheptane

Question 26

Provide the IUPAC name of the compound.

A)2-methylheptane
B)1-chloro-5-methylhexane
C)6-chloro-2-methylhexane
D)1,1-dimethyl-5-chloropentane

Question 27

Give the formula.

A)C₈H₈
B)C₈H₁₀
C)C₈H₁₂
D)C₈H₁₄
E)C₈H₁₆

Question 28

Provide the systematic name of the compound shown.

Question 29

What is the common name for the following structure?

A)Isobutyl bromide
B)t-Butyl bromide
C)Neobutyl bromide
D)sec-Butyl bromide
E)Isopropyl methyl bromide

Question 30

Give the systematic name of the alkane shown below.

Question 31

Provide the common name of the compound.

A)neoheptyl chloride
B)sec-heptyl chloride
C)isoheptyl chloride
D)tert-heptyl chloride
E)n-heptyl chloride

Question 32

Name the compound.

A)2-ethyl-3-propylpentane
B)2,3-diethylhexane
C)4-ethyl-5-methylheptane
D)4-methyl-3-ethylheptane
E)4-ethyl-3-methylheptane

Question 33

Draw an acceptable structure for sec-butylcyclopentane.

Question 34

Give the systematic name of the cycloalkane shown below.

Question 35

Give the IUPAC name for the following compound:

A)1-chloro-2-methylcyclohexane
B)1-methyl-2-chlorocyclohexane
C)1-chloro-5-methylcyclohexane
D)1-methyl-5-chlorocyclohexane
E)1, 2-chloromethylcyclohexane

Question 36

Provide an acceptable name for the compound shown below.

Question 37

Determine the number of hydrogens in limonene.

A)8
B)10
C)12
D)16
E)18

Question 38

Draw all ethers with molecular formula C₄H₁₀O.

Question 39

Provide an acceptable name for the compound shown below.

Question 40

Provide an acceptable name for the compound shown below.

Question 41

Which of the compounds below will form hydrogen bonds between its molecules?

A)CH₃CH₂CH₂F
B)CH₃CH₂CH₂CH₃
C)(CH₃)₃N
D)CH₃CH₂OCH₃
E)CH₃NHCH₂CH₃

Question 42

Provide the systematic name of the compound shown.

Question 43

Draw the structure of 3-chloro-N-ethyl-2-hexanamine.

Question 44

Give the structure of tetramethylammonium chloride.

Question 45

Name the structure.

Question 46

Identify the compound with the highest bond angle.

A)the C-O-C bond in an ether
B)the C-N-C bond in a secondary amine
C)the C-N-C bond in a quaternary amine
D)the C-O-C bond in an alcohol
E)They are all equal.

Question 47

Provide the IUPAC name of the compound.

A)N,N,1,1-tetramethylethanamine
B)N,N-dimethyl-2-butanamine
C)N,N,2-trimethyl-1-propanamine
D)N,N,2-trimethylpropanamine
E)N,N,2-trimethyl-2-propanamine

Question 48

Provide an acceptable name for the compound shown below.

Question 49

Give the structure of isopentyl alcohol.

Question 50

Which of the following compounds does not have the molecular formula C₆H₁₄O?

A)1-hexanol
B)2-hexanol
C)3-methyl-2-pentanol
D)3-methyl-3-pentanol
E)cyclohexanol

Question 51

Provide the common name of the compound.

A)tert-butyldimethylamine
B)isobutyldimethylamine
C)neobutyldimethylamine
D)sec-butyldimethylamine
E)n-butyldimethylamine

Question 52

Identify the compound(s)that do not have hydrogen bonding.

A)CH₃CH₂CH₂NHCH₃
B)CH₃CH₂CH₂CH₂Cl
C)CH₃CH₂CH₂CH₂NH₂
D)CH₃CH₂CH₂CH₂OH
E)CH₃CH₂CH₂OCH₃

Question 53

Classify the following amines as primary, secondary, or tertiary.

Question 54

Provide the IUPAC name of the compound.
H₂NCH₂CH₂CH₂CH₂OH

Question 55

Which of the following will have the lowest boiling point?

A)CH₃Cl
B)CH₄
C)CH₂Cl₂
D)CHCl₃
E)CCl₄

Question 56

Draw the structure of N-ethyl-5-methyl-3-hexanamine.

Question 57

Fluorine is more electronegative than chlorine yet the carbon-fluorine bond in CH₃-F is shorter than CH₃-Cl. Explain.

Question 58

Provide an acceptable name for the compound shown below.

Question 59

Identify the compound with the highest boiling point.

A)CH₃CH₂OCH₂CH₃
B)CH₃CH₂CH₂CH₂OH
C)CH₃CH₂CH₂CH₂NH₂
D)CH₃CH₂CH₂CH₂Cl
E)CH₃CH₂CH₂CH₂Br

Question 60

Give the IUPAC name for the following structure:

A)3-chloro-6-methylcyclohexanol
B)2-methyl-5-chlorocyclohexanol
C)1-chloro-4-methylcyclohexanol
D)5-chloro-2-methylcyclohexanol
E)2-methyl-3-chlorocyclohexanol

Question 61

Primary and secondary amines exhibit hydrogen bonding; tertiary amines do not. Explain.

Question 62

The eclipsed and staggered forms of ethane are said to differ in ________.

A)molecular formula
B)configuration
C)conformation
D)constitution
E)structure

Question 63

Which of the following has the greatest solubility in CH₃CH₂CH₂CH₃?

A)CH₃OH
B)CH₃O^- Na⁺
C)CH₃NH₂
D)CH₃OCH₃
E)(CH₃)₃CH

Question 64

Explain why the molecule shown below has a lower boiling point than CH₃CH₂CH₂CH₃.

Question 65

Which of the molecules below has the higher boiling point? Briefly explain your choice.
CH₃CH₂CH₂OH or CH₃CH₂OCH₃

Question 66

Consider the three isomeric alkanes n-hexane, 2, 3-dimethylbutane, and 2-methylpentane. Which of the following correctly lists these compounds in order of increasing boiling point?

A)2, 3-dimethylbutane < 2-methylpentane < n-hexane
B)2-methylpentane < n-hexane < 2, 3-dimethylbutane
C)2-methylpentane < 2, 3-dimethylbutane < n-hexane
D)n-hexane < 2-methylpentane < 2, 3-dimethylbutane
E)n-hexane < 2, 3-dimethylbutane < 2-methylpentane

Question 67

Which of the following is the staggered conformation for rotation about the C₁-C₂ bond in the following structure?

A)I
B)II
C)III
D)IV
E)V

Question 68

Assuming roughly equivalent molecular weights, which of the following would have the highest boiling point?

A)a tertiary amine
B)a quaternary ammonium salt
C)an alcohol
D)an ether
E)an alkyl chloride

Question 69

Which of the following is the most soluble in H₂O?

A)CH₃OCH₃
B)CH₃CH₂OH
C)CH₃CH₂Cl
D)CH₃CH₂CH₃
E)CH₃CHO

Question 70

What is polarizability and how is it related to the size of an atom?

Question 71

Which of the following has the greatest van der Waal's interaction between molecules of the same kind?

A)
B)CH₃CH₂CH₂CH₃
C)
D)CH₃CH₂CH₂CH₂CH₃
E)

Question 72

Which compound is more soluble in water? Briefly explain your choice.
CH₃OCH₃ or CH₃CH₂OH

Question 73

Which of the following would have the highest boiling point?

A)CH₃CH₂-O-CH₂CH₂-O-CH₃
B)CH₃-O-CH₂CH₂CH₂-O-CH₃
C)HO-CH₂CH₂CH₂CH₂-OH
D)CH₃CH₂-O-CH₂-O-CH₂CH₃
E)

Question 74

Would you expect sodium chloride (NaCl)to be highly soluble in the organic solvent hexane (CH₃CH₂CH₂CH₂CH₂CH₃)? Briefly explain your answer.

Question 75

Which compound is more soluble in water? Briefly explain your choice.
(CH₃)₂NH or CH₃CH₂CH₃

Question 76

What is the strongest intermolecular force present in liquid ethanol?

A)induced dipole-induced dipole
B)dipole-dipole, specifically hydrogen bonding
C)dipole-dipole, but not hydrogen bonding
D)ion-dipole
E)ion-ion

Question 77

Which intermolecular force is primarily responsible for the interactions among alkane molecules?

Question 78

Which of the following has the lowest boiling point?

A)CH₃CH₂CH₂CH₂CH₂CH₃
B)
C)
D)
E)CH₃CH₂CH₂CH₂CH₂CH₂CH₃

Question 79

Arrange the following amines in order of increasing boiling point, lowest bp to highest bp: (CH₃)₂CHCH₂CH₂NH₂, (CH₃)₂CHN(CH₃)₂, and (CH₃)₂CHCH₂NHCH₃.

Question 80

Explain why trimethylamine, (CH₃)₃N:, has a considerably lower boiling point than propylamine CH₃CH₂CH₂NH₂, even though both compounds have the same molecular formula.