Deck 3: An Introduction to Organic Compounds

Question 1

Which of the following is a tertiary amine?

A)
B)
C)
D)
E)

Answer 1

Question 2

Which of the following compounds diisopropyl ether?

A) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { O } - \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 }$
B)
C) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { OCH } \left( \mathrm { CH } _ { 3 } \right) _ { 2 }$
D) $\left( \mathrm { CH } _ { 3 } \right) _ { 3 } \mathrm { COC } \left( \mathrm { CH } _ { 3 } \right) _ { 3 }$
E) $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHOCH}\left(\mathrm{CH}_{3}\right)_{2}$

Answer 2

$\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHOCH}\left(\mathrm{CH}_{3}\right)_{2}$

Question 3

Which of the following is sec-butyl alcohol?

A) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { OH }$
B) $\mathrm { CH } _ { 3 } \mathrm { CH } ( \mathrm { OH } ) \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 }$
C) $\left( \mathrm { CH } _ { 3 } \right) _ { 2 } \mathrm { CHCH } _ { 2 } \mathrm { OH }$
D) $\left( \mathrm { CH } _ { 3 } \right) _ { 2 } \mathrm { CHOH }$
E) $\left( \mathrm { CH } _ { 3 } \right) _ { 2 } \mathrm { CHOCH } _ { 3 }$

Answer 3

$\mathrm { CH } _ { 3 } \mathrm { CH } ( \mathrm { OH } ) \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 }$

Question 4

What is the common name of the following compound?

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

Question 5

How many hydrogens are in limonene?

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

Question 6

There are 8 alkyl bromides with a molecular formula of C₅H₁₁Br. How many of these are tertiary alkyl bromides?

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

Question 7

How many constitutional isomers have a molecular formula of C₆H₁₄?

A) 4
B) 5
C) 6
D) 7
E) 8

Question 8

Which of the following compounds has the highest boiling point?

A) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { OCH } _ { 2 } \mathrm { CH } _ { 3 }$
B) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { OH }$
C) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { NH } _ { 2 }$
D) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Cl }$
E) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Br }$

Question 9

What is the name of the following 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 10

What is the name of 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, k2-chloromethylcyclohexane

Question 11

What is the name of the following 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 12

Which of the following compounds cannot form hydrogen bonds between its molecules?

A) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { NHCH } _ { 3 }$
B) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Cl }$
C) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { NH } _ { 2 }$
D) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { OH }$
E) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { OCH } _ { 3 }$

Question 13

What is the IUPAC name of the following compound?

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

Question 14

Which of the following has the largest bond angle?

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

Question 15

What is the common name of the following compound?

A) isobutane
B) isopropylmethane
C) tert-butane
D) n-butane
E) sec-butane

Question 16

How many tertiary carbons are in the following compound?

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

Question 17

What is the name of the following compound?

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

Question 18

What is the molecular formula of the following compound?

A) $\mathrm { C } _ { 8 } \mathrm { H } _ { 8 }$
B) $\mathrm { C } _ { 8 } \mathrm { H } _ { 10 }$
C) $\mathrm { C } _ { 8 } \mathrm { H } _ { 12 }$
D) $\mathrm { C } _ { 8 } \mathrm { H } _ { 14 }$
E) $\mathrm { C } _ { 8 } \mathrm { H } _ { 16 }$

Question 19

What is the common name of the following compound?

A) Isobutyl bromide
B) $t \text {-Butyl bromide }$
C) Neobutyl bromide
D) $\text { sec-Butyl bromide }$
E) Isopropyl methyl bromide

Question 20

If an acyclic alkane contains n carbons, how many hydrogens does it contain?

A) n
B) n+2
C) n-2
D) 2n
E) 2n + 2

Question 21

Which of the following is a staggered conformer for rotation about the Cl-C2 bond in the following compound?

I.

II.

III.

IV.

V.

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

Question 22

Which of the following is the most stable conformer of bromocyclohexane? I.

II.

III.

IV.

V.

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

Question 23

Which of the following compounds has the greatest van der Waal's interactions between its molecules?

A)
B) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 }$
C)
D) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 }$
E)

Question 24

Assuming roughly equivalent molecular weights, which of the following compounds has the highest boiling point?

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

Question 25

Which of the following describes the most stable conformer of $$\text { trans-1-tert-butyl-3- }$$ methylcyclohexane?

A) Both groups are equatorial.
B) Both groups are axial.
C) The tert-butyl group is equatorial and the methyl group is axial.
D) The tert-butyl group is axial and the methyl group is equatorial.
E) none of the above

Question 26

Which conformer has the greatest energy in the potential energy diagram for chair-chair interconversion of cyclohexane?

A) twist-boat
B) planar
C) boat
D) half-chair
E) chair

Question 27

Which of the following compounds has the highest boiling point?

A) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } - \mathrm { O } - \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { O } - \mathrm { CH } _ { 3 }$
B) $\mathrm { CH } _ { 3 } - \mathrm { O } - \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { O } - \mathrm { CH } _ { 3 }$
C) $\mathrm { HO } - \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { OH }$
D) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } - \mathrm { O } - \mathrm { CH } _ { 2 } - \mathrm { O } - \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 }$
E)

Question 28

Which of the following compounds cannot form hydrogen bonds between its molecules?

A) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm {~F}$
B) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 }$
C) $\left( \mathrm { CH } _ { 3 } \right) _ { 3 } \mathrm {~N}$
D) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { OCH } _ { 3 }$
E) $\mathrm { CH } _ { 3 } \mathrm { NHCH } _ { 2 } \mathrm { CH } _ { 3 }$

Question 29

Identify the relative positions of the methyl groups in the most stable conformer of butane viewed along th C2-C3 bond?

A) anti
B) eclipsed
C) gauche
D) totally eclipsed
E) adjacent

Question 30

Which of the following compounds is the most soluble H₂CO?

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

Question 31

The eclipsed and staggered forms of ethane differ in ________.

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

Question 32

List n-hexane, 2, 3-dimethylbutane, and 2-methylpentane in order of increasing boiling point.

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

Question 33

Which of the following statements about the conformers that result from rotation about the C2-C3 bond of butane is correct?

A) The highest energy conformer is one in which methyl groups are eclipsed by hydrogens.
B) The gauche conformer is eclipsed.
C) Steric strain is absent in an eclipsed conformer.
D) An eclipsed conformer is more stable than a staggered conformer.
E) none of the above

Question 34

Which of the following compounds has the lowest boiling point?

A) CH₃Cl
B) CH₄
C) CH₂Cl₂
D) CHCl₃
E) CCl₄

Question 35

Which of the following correctly ranks the cycloalkanes in order of increasing ring strain?

A) cyclopropane < cyclobutane < cyclohexane < cycloheptane
B) cyclohexane < cyclopentane < cyclobutane < cyclopropane
C) cyclopentane < cyclobutane < cyclopentane < cyclopropane
D) cyclopentane < cyclopropane < cyclobutane < cyclohexane
E) cyclopropane < cyclopentane < cyclobutane < cyclohexane

Question 36

What is the strongest intermolecular force between molecules of ethyl alcohol?

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 37

Which of the following correctly lists the conformers of cyclohexane in order of increasing energy?

A) chair < boat < twist-boat < half-chair
B) half-chair < boat < twist-boat < chair
C) chair < twist-boat < half-chair < boat
D) chair < twist-boat < boat < half-chair
E) half-chair < twist-boat < boat < chair

Question 38

Which conformers of butane, viewed along the Cl-C2 bond, has the lowest energy?

A) the gauche conformer
B) the eclipsed and gauche conformers
C) the anti conformer
D) the eclipsed conformer
E) the anti and gauche conformers

Question 39

Which of the following compounds has the lowest boiling point?

A) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 }$
B)
C)
D)
E) CH₃CH₂CH₂CH₂CH₂CH₂CH₃

Question 40

Which of the following has the greatest solubility $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 }$ ?

A) $\mathrm { CH } _ { 3 } \mathrm { OH }$
B) $\mathrm { CH } _ { 3 } \mathrm { O } ^ { - } \mathrm { Na } ^ { + }$
C) $\mathrm { CH } _ { 3 } \mathrm { NH } _ { 2 }$
D) $\mathrm { CH } _ { 3 } \mathrm { OCH } _ { 3 }$
E) $\left( \mathrm { CH } _ { 3 } \right) _ { 3 } \mathrm { CH }$

Question 41

How many secondary hydrogens does the following compound have?

A) 4
B) 6
C) 8
D) 10
E) 12

Question 42

Which of the following is the least the least stable conformer of 1-tert-butyl-3- methylcyclohexane.

A) tert-butyl is axial and the methyl is equatorial.
B) tert-butyl is axial and the methyl is axial.
C) tert-butyl is equatorial and the methyl is axial.
D) tert-butyl is equatorial and the methyl is equatorial.
E) All are equally stable.

Question 43

Draw 6-ethyl-2,6,7-trimethyl-5-propylnonane.

Question 44

Name the alkane shown below.

Question 45

Which of the following has a conformer with two equatorial alkyl substituents?

A) 1,1 -dimethylcyclohexane
B) cis-1,2-dimethylcyclohexane
C) cis-1,3-diethylcyclohexane
D) cis-1,4-diethylcyclohexane
E) trans-1,3-diethylcyclohexane

Question 46

How many hydrogens are attached to the indicated carbon?

A) zero
B) one
C) two
D) three

Question 47

Name the alkane shown below.

Question 48

Does this Newman projection depict the conformer of the molecule with the lowest-energy?

A) Yes
B) No
C) There is not enough information to tell.

Question 49

Draw 4-isopropyl-2-methylheptane.

Question 50

Name the alkane shown below.

Question 51

Name the alkane shown below.

Question 52

2-Ethylpropane is not a correct name. Draw the compound and name it correctly.

Question 53

Name the alkane shown below.

Question 54

How many hydrogens are attached to the indicated carbon?

A) zero
B) one
C) two
D) three

Question 55

Name the compound shown below.

A) trans-1,2-dichlorocyclohexane
B) cis-1,2-dichlorocyclohexane
C) trans-1,3-dichlorocyclohexane
D) cis-1,3-dichlorocyclohexane
E) trans-1,4 -dichlorocyclohexane

Question 56

Name the alkane shown below.

Question 57

Draw 3-ethyl-3-methylhexane.

Question 58

Draw 4-tert-butyloctane.

Question 59

How many hydrogens are attached to the indicated carbon?

A) zero
B) one
C) two
D) three

Question 60

Which of the following has a conformer with one equatorial substituent and one axial substituent?

A) trans-1,4-dibromocyclohexane
B) cis-1,4-dibromocyclohexane
C) cis-1,3-dibromocyclohexane
D) trans-1,2-dibromocyclohexane
E) none of them

Question 61

Name the cycloalkane shown below.

Question 62

Draw the structure for isopentyl alcohol.

Question 63

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

Question 64

Explain why the carbon-fluorine bond in is shorter than the carbon-chlorine bond in .

Question 65

Name the compound shown below.

Question 66

Which of the compounds shown below has the higher boiling point? Explain your choice. CH₃CH₂CH₂OH or CH₃CH₂OCH₃

Question 67

Name the alkane shown below.

Question 68

Name the alkane shown below.

Question 69

Would you expect sodium chloride (NaCl) to be soluble in hexane? Explain your answer.

Question 70

Draw all ethers with molecular formula C₄H₁₀O.

Question 71

Name the compound shown below.

Question 72

Draw all possible constitutional isomers for C₂H₆O and give a common name for each isomer.

Question 73

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

Question 74

Explain why primary and secondary amines form hydrogen bonds but tertiary amines do not.

Question 75

Name the alkane shown below.

Question 76

Name the compound shown below.

Question 77

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

Question 78

Name the alkane shown below.

Question 79

Draw the structure for sec-butylcyclopentane.

Question 80

Explain why trimethylamine, , has a considerably lower boiling point than
propylamine , even though both compounds have the same molecular formula.