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ISBN-10: 0321596951

ISBN-13: 9780321596956

Essential Organic Chemistry 2nd Edition By Bruice – Test Bank 

 

Essential Organic Chemistry, 2e (Bruice)

 

Chapter 1

 

 

Electronic Structure and Covalent Bonding

 

1)

 

Atoms with the same number of protons but different numbers of neutrons are called __________.

 

Answer:

 

isotopes

 

Section:

 

 

1.1

 

2)

 

What isotope of chlorine has the same number of neutrons as Argon-38?

 

  1. A)

 

17Cl

 

  1. B)

 

35Cl

 

  1. C)

 

36Cl

 

  1. D)

 

37Cl

 

  1. E)

 

38Cl

 

Answer:

 

D

 

Section:

 

 

1.1

 

3)

 

Which statement is incorrect about the atomic number of an atom?

 

  1. A)

 

It equals the number of protons in its nucleus.

 

  1. B)

 

It equals the number of electrons outside the nucleus.

 

  1. C)

 

It equals the sum of its protons and neutrons..

 

  1. D)

 

It is a whole number.

 

  1. E)

 

It is given on the Periodic Table.

 

Answer:

 

C

 

Section:

 

 

1.1

 

4)

 

Which of the following elements does this electronic configuration represent?

1s2 2s2 2p5

 

 

  1. A)

 

F

 

  1. B)

 

C

 

  1. C)

 

N

 

  1. D)

 

Al

 

  1. E)

 

O

 

Answer:

 

A

 

Section:

 

 

1.2

 

5)

 

Which of the following is the electronic configuration of the element Fe?

 

  1. A)

 

1s2 2s2 2p6 3s2 3p6 4s2 3d6

 

  1. B)

 

1s2 2s2 2p6 3s2 3p8 3d6

 

  1. C)

 

1s2 2s2 2p8 3s2 3p6 4s2 3d6

 

  1. D)

 

1s2 2s2 2p6 3s2 3p6 4s2 4d6

 

  1. E)

 

1s2 2s2 2p6 3s2 3p6 4s2 4p6

 

Answer:

 

A

 

Section:

 

 

1.2

 

6)

 

Ar, K+, Cl- are isoelectronic elements (elements with the same number of electrons). What orbital does the last electron occupy?

 

Answer:

 

3p orbital

 

Section:

 

 

1.2

 

7)

 

The atomic number of boron is 5. The correct electronic configuration of boron is __________.

 

  1. A)

 

1s2 2s3

 

  1. B)

 

1s2 2p3

 

  1. C)

 

1s2 2s2 2p1

 

  1. D)

 

2s2 2p3

 

  1. E)

 

1s2 2s2 3s1

 

Answer:

 

C

 

Section:

 

 

1.2

 

8)

 

Which of the following statements correctly describes the third electron shell that surrounds the nucleus of an atom?

 

  1. A)

 

The third shell contains only s and p atomic orbitals.

 

  1. B)

 

The maximum number of electrons that can occupy the third shell is 18.

 

  1. C)

 

The total number of atomic orbitals present in the third shell is 16.

 

  1. D)

 

The third shell can contain f orbitals.

 

  1. E)

 

none of the above

 

Answer:

 

B

 

Section:

 

 

1.2

 

9)

 

Which of the following describes a hydride ion?

 

  1. A)

 

a negatively charged hydrogen ion containing a pair of electrons

 

  1. B)

 

a positively charged hydrogen ion

 

  1. C)

 

a hydrogen ion containing a single electron

 

  1. D)

 

a negatively charged OH ion

 

  1. E)

 

a proton containing an extra electron

 

Answer:

 

A

 

Section:

 

 

1.3

 

10)

 

Rank the following atoms in increasing electronegativity.

 

  1. A)

 

N, Na, Si, O, C

 

  1. B)

 

C, N, O, Na,  Si

 

  1. C)

 

O, N, C, Si, Na

 

  1. D)

 

Si, C, N, O, Na

 

  1. E)

 

Na, Si, C, N, O

 

Answer:

 

E

 

Section:

 

 

1.3

 

11)

 

Using the symbol δ+ and δ-, indicate the direction of the polarity in the indicated bond.

 

 

 

Answer:

 

 

 

 

Section:

 

 

1.3

 

12)

 

Covalent bonds may be polar or nonpolar. What property of the atoms forming a given bond accounts for this fact?

 

Answer:

 

electronegativity

 

Section:

 

 

1.3

 

13)

 

The compound methylamine, H3C-NH2, contains a C-N bond. In this bond, which of the following best describes the charge on the nitrogen atom?

 

  1. A)

 

+1

 

  1. B)

 

slightly positive

 

  1. C)

 

uncharged

 

  1. D)

 

slightly negative

 

  1. E)

 

-1

 

Answer:

 

D

 

Section:

 

 

1.3

 

14)

 

Which of the compounds below bond predominantly via ionic bonding?

 

  1. A)

 

KCl

 

  1. B)

 

CF4

 

  1. C)

 

NH3

 

  1. D)

 

both A and B

 

  1. E)

 

both B and C

 

Answer:

 

A

 

Section:

 

 

1.3

 

15)

 

What type of bonding is most important in CH3CH2CH2CH2CH2CH3?

 

  1. A)

 

ionic

 

  1. B)

 

hydrogen

 

  1. C)

 

covalent

 

  1. D)

 

polar

 

Answer:

 

C

 

Section:

 

 

1.3

 

16)

 

Which of the following contains polar covalent bonds?

 

  1. A)

 

NH3

 

  1. B)

 

Na2O

 

  1. C)

 

H2

 

  1. D)

 

KF

 

  1. E)

 

both A and C

 

Answer:

 

A

 

Section:

 

 

1.3

 

17)

 

What is the name given for a species that contains a positively charged carbon atom?

 

  1. A)

 

carbanion

 

  1. B)

 

carbocation

 

  1. C)

 

methyl radical

 

  1. D)

 

carbon radical

 

  1. E)

 

free radical

 

Answer:

 

B

 

Section:

 

 

1.4

 

18)

 

Which of the following is the most likely (i.e., most stable) electronic structure for C2H2?

 

  1. A)

 

 

 

 

  1. B)

 

 

 

 

  1. C)

 

 

 

 

  1. D)

 

HCCH

 

 

  1. E)

 

 

 

 

Answer:

 

D

 

Section:

 

 

1.4

 

19)

 

Which of the following structures, including formal charges, is correct for diazomethane, H2CN2?

 

  1. A)

 

: H2CNN:

 

 

  1. B)

 

 

 

 

  1. C)

 

 

 

 

  1. D)

 

 

 

 

  1. E)

 

 

 

 

Answer:

 

D

 

Section:

 

 

1.4

 

20)

 

What are the formal charges on nitrogen and the starred oxygen atom in the following molecule?

 

 

 

  1. A)

 

N = -1, O = 0

 

  1. B)

 

N = +1, O = -1

 

  1. C)

 

N = +1, O = +1

 

  1. D)

 

N = -1, O = -1

 

  1. E)

 

N= +1, O = 0

 

Answer:

 

E

 

Section:

 

 

1.4

 

21)

 

Draw the Kekulé structure for each of the following:

  1. CH3CH2OH b.    CH3CHO             c.     (CH3)3C+

 

Answer:

 

 

 

 

Section:

 

 

1.4

 

22)

 

What is the formal charge on the phosphorus in the PO43- polyatomic ion?

 

  1. A)

 

-3

 

  1. B)

 

-2

 

  1. C)

 

-1

 

  1. D)

 

0

 

  1. E)

 

+1

 

Answer:

 

E

 

Section:

 

 

1.4

 

23)

 

The formal charge on nitrogen in the compound below is __________.

 

 

 

  1. A)

 

+2

 

  1. B)

 

+1

 

  1. C)

 

0

 

  1. D)

 

-1

 

  1. E)

 

-2

 

Answer:

 

B

 

Section:

 

 

1.4

 

24)

 

The Kekulé structure of pentane is shown below. Draw the condensed structural formula which corresponds to this Lewis structure.

 

 

 

Answer:

 

CH3(CH2)3CH3

 

Section:

 

 

1.4

 

25)

 

Draw condensed structures for the four compounds with formula C3H9N.

 

Answer:

 

CH3CH2CH2NH2

CH3CH2NHCH3

(CH3)2CHNH2

(CH3)3N

 

Section:

 

 

1.4

 

26)

 

Write a Lewis structure for the molecule given below.

 

CH2O

 

Answer:

 

 

 

 

Section:

 

 

1.4

 

27)

 

Expand the condensed structure below to show the covalent bonds and the lone-pair electrons.

 

(CH3)2CHCH2CHO

 

Answer:

 

 

 

 

Section:

 

 

1.4

 

28)

 

Draw the shape of a 2p orbital.

 

Answer:

 

 

 

 

Section:

 

 

1.5

 

29)

 

What is the name given to a three-dimensional region where an electron is found?

 

  1. A)

 

nucleus

 

  1. B)

 

ion

 

  1. C)

 

sphere

 

  1. D)

 

orbital

 

  1. E)

 

cloud

 

Answer:

 

D

 

Section:

 

 

1.5

 

30)

 

How many distinct p orbitals exist in the second electron shell?

 

  1. A)

 

0

 

  1. B)

 

1

 

  1. C)

 

2

 

  1. D)

 

3

 

  1. E)

 

4

 

Answer:

 

D

 

Section:

 

 

1.5

 

31)

 

Which describes the bond strength or bond dissociation energy?

 

  1. A)

 

energy required to break a bond

 

  1. B)

 

energy released when a bond breaks

 

  1. C)

 

energy released when a bond is formed

 

  1. D)

 

A and B

 

  1. E)

 

A and C

 

Answer:

 

E

 

Section:

 

 

1.6

 

32)

 

Which statement is correct?

 

  1. A)

 

Energy is released when a bond breaks.

 

  1. B)

 

A sigma bond results from attraction of protons and electrons.

 

  1. C)

 

Energy is released when a bond forms.

 

  1. D)

 

Protons and electrons are repulsive.

 

  1. E)

 

A carbanion is positively charged.

 

Answer:

 

C

 

Section:

 

 

1.6

 

33)

 

Both sigma (σ) and pi (π) bonds can be formed by overlapping p orbitals. Describe the difference.

 

Answer:

 

Sigma bonds are formed from the overlap of atomic orbitals along a circular axis of symmetrical nature, i.e., head-on overlap. All single bonds are sigma bonds.

 

Pi bonds are formed from the overlap of atomic orbitals along a non-symmetrical (parallel) axis, i.e., side-to-side overlap. Double and triple bonds are pi bonds.

 

Section:

 

 

1.6 and 1.8

 

34)

 

Choose the correct hybridization for the atom indicated in the molecule below.

 

CH3CH2CH2CH3

 

  1. A)

 

sp

 

  1. B)

 

sp2

 

  1. C)

 

sp3

 

  1. D)

 

none of the above

 

Answer:

 

C

 

Section:

 

 

1.7

 

35)

 

What orbitals are used to form the covalent bonds in butane (CH3CH2CH2CH3)?

 

Answer:

 

The carbon-carbon σ bonds are formed by the overlap of two carbon sp3 hybrid atomic orbitals. The carbon-hydrogen σ bonds are formed by the overlap of a carbon sp3 hybrid atomic orbital and a hydrogen s orbital.

 

Section:

 

 

1.7

 

36)

 

Which of the following is a nonpolar molecule?

 

  1. A)

 

HCl

 

  1. B)

 

CH3Cl

 

  1. C)

 

H2

 

  1. D)

 

CO

 

  1. E)

 

NH3

 

Answer:

 

C

 

Section:

 

 

1.3 and 1.7

 

37)

 

Which of the following is a correct formula for a compound?

 

  1. A)

 

CH3CH2(CH3)2CH2CH3

 

  1. B)

 

CH2CH2(CH3)CH2CH3

 

  1. C)

 

CH3CH(CH3)CH2CH3

 

  1. D)

 

CH3CH2(CH3)2

 

  1. E)

 

C

 

Answer:

 

C

 

Section:

 

 

1.7

 

38)

 

Which of the following results from the combining of atomic orbitals?

 

  1. A)

 

s orbital

 

  1. B)

 

nonpolar molecule

 

  1. C)

 

hybrid orbitals

 

  1. D)

 

polar molecule

 

  1. E)

 

sigma bond

 

Answer:

 

C

 

Section:

 

 

1.7

 

39)

 

How many electrons are involved in a carbon-carbon double bond?

 

  1. A)

 

1

 

  1. B)

 

2

 

  1. C)

 

3

 

  1. D)

 

4

 

  1. E)

 

5

 

Answer:

 

D

 

Section:

 

 

1.8

 

40)

 

Which of the following describes a triple bond?

 

  1. A)

 

two sigma bonds and two pi bonds

 

  1. B)

 

three pi bonds

 

  1. C)

 

one sigma bond and one pi bond

 

  1. D)

 

two sigma bonds and one pi bond

 

  1. E)

 

one sigma bond and two pi bonds

 

Answer:

 

E

 

Section:

 

 

1.9

 

41)

 

Which carbon(s) in the following molecule is (are) sp hybridized?

 

 

 

  1. A)

 

carbon 1

 

  1. B)

 

carbon 2

 

  1. C)

 

carbon 1, 3

 

  1. D)

 

carbon 4

 

  1. E)

 

carbon 4, 5

 

Answer:

 

E

 

Section:

 

 

1.9

 

42)

 

Which of the following is an sp2 hybridized carbon?

 

  1. A)

 

 

 

  1. B)

 

∙ CH3

 

  1. C)

 

 

 

  1. D)

 

A and B

 

  1. E)

 

A, B and C

 

Answer:

 

A

 

Section:

 

 

1.10

 

43)

 

What orbitals overlap to create the H-C bond in CH3+?

 

  1. A)

 

sp3-sp3

 

  1. B)

 

sp2-sp3

 

  1. C)

 

sp

 

  1. D)

 

ssp2

 

  1. E)

 

ssp3

 

Answer:

 

D

 

Section:

 

 

1.10

 

44)

 

The lone-pair electrons of the methyl anion occupy a __________ orbital.

 

  1. A)

 

s

 

  1. B)

 

p

 

  1. C)

 

sp

 

  1. D)

 

sp2

 

  1. E)

 

sp3

 

Answer:

 

E

 

Section:

 

 

1.10

 

45)

 

Explain why the water molecule has a bent shape and a bond angle less than 109.5°.

 

Answer:

 

The electron replusion between the two lone pairs of electrons on the oxygen of water causes the O-H bonds to squeeze close together.

 

Section:

 

 

1.11

 

46)

 

Which of the following is closest to the C-O-C bond angle in CH3-O-CH3?

 

  1. A)

 

180°

 

  1. B)

 

120°

 

  1. C)

 

109.5°

 

  1. D)

 

90°

 

  1. E)

 

160°

 

Answer:

 

C

 

Section:

 

 

1.11

 

47)

 

Triethylamine [(CH3CH2)3N] is a molecule in which the nitrogen atom is __________ hybridized and the CNC bond angle is __________.

 

  1. A)

 

sp2; >109.5°

 

  1. B)

 

sp2; <109.5°

 

  1. C)

 

sp3; >109.5°

 

  1. D)

 

sp3; <109.5°

 

  1. E)

 

sp; 109.5°

 

Answer:

 

D

 

Section:

 

 

1.12

 

48)

 

The N-H bond in the ammonium ion, NH4+, is formed by the overlap of what two orbitals?

 

  1. A)

 

sp3-sp3

 

  1. B)

 

sp3-sp2

 

  1. C)

 

sp2-sp2

 

  1. D)

 

sp2-s

 

  1. E)

 

sp3-s

 

Answer:

 

E

 

Section:

 

 

1.12

 

49)

 

Among the hydrogen halides, the strongest bond is found in __________ and the longest bond is found in __________.

 

  1. A)

 

HF; HF

 

  1. B)

 

HF; HI

 

  1. C)

 

HI; HF

 

  1. D)

 

HI; HI

 

  1. E)

 

HCl; HBr

 

Answer:

 

B

 

Section:

 

 

1.13

 

50)

 

Which bond in the following molecule is the shortest?

 

 

 

  1. A)

 

bond 1

 

  1. B)

 

bond 2

 

  1. C)

 

bond 3

 

  1. D)

 

bond 4

 

  1. E)

 

bond 5

 

Answer:

 

E

 

Section:

 

 

1.14

 

51)

 

Which of the following species have tetrahedral bond angles?

 

 

 

  1. A)

 

A, D and E

 

  1. B)

 

A, D, E and F

 

  1. C)

 

A and E

 

  1. D)

 

D only

 

  1. E)

 

A, B and E

 

Answer:

 

B

 

Section:

 

 

1.14

 

52)

 

The carbon-carbon double bond in ethene is __________ and __________ than the carbon-carbon triple bond in ethyne.

 

  1. A)

 

stronger; shorter

 

  1. B)

 

stronger; longer

 

  1. C)

 

weaker; shorter

 

  1. D)

 

weaker; longer

 

  1. E)

 

stronger; more polar

 

Answer:

 

D

 

Section:

 

 

1.14

 

53)

 

Draw the structure of a molecule which contains only carbon and hydrogen atoms (only three of which are carbon) and in which two of the carbons are sp2 hybridized and the other is sp hybridized.

 

Answer:

 

H2CCCH2

 

Section:

 

 

1.14

 

54)

 

What is the CNN bond angle in the compound shown below?

 

 

 

  1. A)

 

~60°

 

  1. B)

 

~90°

 

  1. C)

 

~110°

 

  1. D)

 

~120°

 

  1. E)

 

~180°

 

Answer:

 

D

 

Section:

 

 

1.14

 

55)

 

Why is the CH bond in ethene (H2CCH2) shorter and stronger than the CH bond in ethane(H3C-CH3)?

 

Answer:

 

The length and strength of a CH bond depends on the hybridization of the carbon atom. The more s character in the hybrid orbital used by carbon to form the bond, the shorter and stronger the bond. This is because an s orbital is closer to the nucleus than is a p  orbital. Ethene uses carbon sp2 hybridized orbitals (1/3 s character) to make its carbon-hydrogen bonds while ethane uses carbon sp3 (1/4 s character) orbitals.

 

Section:

 

 

1.14

 

56)

 

What is the predicted shape, bond angle, and hybridization for +CH3?

 

  1. A)

 

trigonal planar, 120°, sp2

 

  1. B)

 

trigonal planar, 120°, sp3

 

  1. C)

 

trigonal planar, 109.5°, sp2

 

  1. D)

 

trigonal pyramidal, 120°, sp2

 

  1. E)

 

trigonal pyramidal, 109.5°, sp2

 

Answer:

 

A

 

Section:

 

 

1.8, 1.10, and 1.14

 

Essential Organic Chemistry, 2e (Bruice)

 

Chapter 3

 

 

An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Representation of Structure

 

1)

 

Explain what is meant by the term “saturated hydrocarbons.”

 

Answer:

 

These are compounds containing only single bonded carbons and hydrogens where each carbon has the maximum number of hydrogens bonded to it. The alkanes are saturated hydrocarbons.

 

Section:

 

 

3.0

 

2)

 

Describe the carbon-carbon bond differences between alkanes, alkene, and alkynes.

 

Answer:

 

Alkanes contain only carbon-carbon single bonds. Alkenes contain at least one carbon-carbon double bond. Alkynes contain at least one carbon-carbon triple bond.

 

Section:

 

 

3.0

 

3)

 

Explain the relationship between alkanes and gasoline.

 

Answer:

 

Petroleum is a complex mixture of alkanes and cycloalkanes that are separated into different fractions by distillation. 5 to 11-carbon alkanes are used for gasoline. Straight-chain alkanes  are poor fuels so catalytic cracking is used to convert these straight-chain alkanes  into branched-chain alkanes which are high-performance fuels.

 

Section:

 

 

3.0

 

4)

 

Explain why alkanes are generally considered unreactive compounds.

 

Answer:

 

They are unreactive because they have only strong σ bonds and atoms which have no partial charges.

 

Section:

 

 

3.0

 

5)

 

Which of the following is the best description of propane, CH3CH2CH3, at room temperature?

 

  1. A)

 

liquid, soluble in H2O

 

  1. B)

 

gas, soluble in gasoline

 

  1. C)

 

liquid, soluble in gasoline

 

  1. D)

 

gas, soluble in water

 

  1. E)

 

solid, soluble in gasoline

 

Answer:

 

B

 

Section:

 

 

3.1

 

6)

 

The following molecule contains how many 1°, 2°, and 3° hydrogens?

 

 

 

Answer:

 

12 =1°, 6 =2°, 2 =3°

 

Section:

 

 

3.1

 

7)

 

Which of the following is a tertiary amine?

 

  1. A)

 

 

 

 

  1. B)

 

 

 

 

  1. C)

 

 

 

 

  1. D)

 

 

 

 

  1. E)

 

 

 

 

Answer:

 

E

 

Section:

 

 

3.1 and 3.5

 

8)

 

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

 

  1. A)

 

0

 

  1. B)

 

1

 

  1. C)

 

2

 

  1. D)

 

3

 

  1. E)

 

8

 

Answer:

 

B

 

Section:

 

 

3.1

 

9)

 

Draw the structure for 3-ethyl-5-isobutyldecane.

 

Answer:

 

 

 

 

 

Section:

 

 

3.1

 

10)

 

Which of the following is sec-butyl alcohol?

 

  1. A)

 

CH3CH2CH2CH2OH

 

  1. B)

 

CH3CH(OH)CH2CH3

 

  1. C)

 

(CH3)2CHCH2OH

 

  1. D)

 

(CH3)2CHOH

 

  1. E)

 

(CH3)2CHOCH3

 

Answer:

 

B

 

Section:

 

 

3.1

 

11)

 

How should (CH3)2C(OH)CH2CH3 be classified?

 

  1. A)

 

primary alcohol

 

  1. B)

 

secondary alcohol

 

  1. C)

 

tertiary alcohol

 

  1. D)

 

quarternary alcohol

 

  1. E)

 

none of the above

 

Answer:

 

C

 

Section:

 

 

3.1 and 3.5

 

12)

 

How should CH3CHClCH2CH3 be classified?

 

  1. A)

 

primary alkyl halide

 

  1. B)

 

secondary alkyl halide

 

  1. C)

 

tertiary alkyl halide

 

  1. D)

 

quarternary alkyl halide

 

  1. E)

 

pentanary alkyl halide

 

Answer:

 

B

 

Section:

 

 

3.1 and 3.5

 

13)

 

What is the common name for the following structure?

 

 

 

  1. A)

 

Isobutane

 

  1. B)

 

Isopropylmethane

 

  1. C)

 

t-Butane

 

  1. D)

 

n-Butane

 

  1. E)

 

sec-Butane

 

Answer:

 

A

 

Section:

 

 

3.2

 

14)

 

Give the IUPAC name for the following structure:

 

 

  1. A)

 

2-methyl-3-ethylheptane

 

  1. B)

 

3-ethyl-2-methylheptane

 

  1. C)

 

5-Isopropyloctane

 

  1. D)

 

4-Isopropyloctane

 

  1. E)

 

2-methyl-3-propylheptane

 

Answer:

 

D

 

Section:

 

 

3.2

 

15)

 

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

 

Answer:

 

 

The correct name is 2-methylbutane.

 

Section:

 

 

3.2

 

16)

 

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

 

Answer:

 

 

 

 

Section:

 

 

3.2

 

17)

 

Provide an acceptable name for the alkane shown below.

 

CH3CH2CH2CH2CH2CH3

 

Answer:

 

hexane or n-hexane

 

Section:

 

 

3.2

 

18)

 

Provide an acceptable name for the alkane shown below.

 

 

 

Answer:

 

2,5-dimethylheptane

 

Section:

 

 

3.2

 

19)

 

Provide an acceptable name for the alkane shown below.

 

 

 

Answer:

 

5-sec-butyl-2,2-dimethylnonane or

2,2-dimethyl-5-(1-methylpropyl) nonane

 

Section:

 

 

3.2

 

20)

 

Provide an acceptable name for the alkane shown below.

 

 

 

Answer:

 

4-isopropyldecane or 4-(1-methlyethyl) decane

 

Section:

 

 

3.2

 

21)

 

Provide an acceptable name for the alkane shown below.

 

 

 

Answer:

 

3-ethyl-6-methyl-5-propylnonane

 

Section:

 

 

3.2

 

22)

 

Provide an acceptable name for the alkane shown below.

 

 

 

Answer:

 

3-Ethyl-4, 4-dimethylheptane

 

Section:

 

 

3.2

 

23)

 

Draw an acceptable structure for 4-t-butyloctane.

 

Answer:

 

 

 

 

Section:

 

 

3.2

 

24)

 

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

 

Answer:

 

 

 

 

Section:

 

 

3.2

 

25)

 

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

 

Answer:

 

 

 

 

Section:

 

 

3.2

 

26)

 

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

 

Answer:

 

 

 

 

Section:

 

 

3.2

 

27)

 

Provide an acceptable name for the alkane shown below.

 

 

 

Answer:

 

2,2,3,6-tetramethylheptane

 

Section:

 

 

3.2

 

28)

 

Provide an acceptable name for the alkane shown below.

 

 

 

Answer:

 

6-ethyl-2-methyl-5-propyldecane

 

Section:

 

 

3.2

 

29)

 

Give the systematic name of the alkane shown below.

 

 

 

Answer:

 

4-ethyl-2,2,7-trimethylnonane

 

Section:

 

 

3.2

 

30)

 

Give the systematic name of the alkane shown below.

 

 

 

Answer:

 

3-ethyl-4-isopropyloctane

 

Section:

 

 

3.2

 

31)

 

Give the systematic name of the cycloalkane shown below.

 

 

 

Answer:

 

4-butyl-1,2-dimethylcyclohexane

 

Section:

 

 

3.3

 

32)

 

Draw an acceptable structure for sec-butylcyclopentane.

 

Answer:

 

 

 

 

Section:

 

 

3.3

 

33)

 

What is the common name for the following structure?

 

 

 

  1. A)

 

Isobutyl bromide

 

  1. B)

 

t-Butyl bromide

 

  1. C)

 

Neobutyl bromide

 

  1. D)

 

sec-Butyl bromide

 

  1. E)

 

Isopropyl methyl bromide

 

Answer:

 

B

 

Section:

 

 

3.4

 

34)

 

Give the IUPAC name for the following compound:

 

 

 

  1. A)

 

1-chloro-2-methylcyclohexane

 

  1. B)

 

1-methyl-2-chlorocyclohexane

 

  1. C)

 

1-chloro-5-methylcyclohexane

 

  1. D)

 

1-methyl-5-chlorocyclohexane

 

  1. E)

 

1,2-chloromethylcyclohexane

 

Answer:

 

A

 

Section:

 

 

3.4

 

35)

 

Draw the structure for 3-iodo-5-isopropyl-3,4-dimethylheptane

 

Answer:

 

 

 

 

 

Section:

 

 

3.4

 

36)

 

Draw the structure for 2-chloro-3-ethylpentane

 

Answer:

 

 

 

 

 

Section:

 

 

3.4

 

37)

 

Draw the structure of 2,3-dibromo-2-methylbutane.

 

Answer:

 

 

 

 

 

Section:

 

 

3.4

 

38)

 

How is the structure shown below classified?

 

 

 

  1. A)

 

a primary alkyl halide

 

  1. B)

 

a primary alcohol

 

  1. C)

 

a secondary alkyl halide

 

  1. D)

 

a secondary alcohol

 

  1. E)

 

a tertiary alkyl halide

 

Answer:

 

C

 

Section:

 

 

3.5

 

39)

 

How is the structure shown below classified?

 

 

  1. A)

 

a quarternary ammonium ion

 

  1. B)

 

a quarternary amine

 

  1. C)

 

a secondary amine

 

  1. D)

 

a primary amine

 

  1. E)

 

a tertiary amine

 

Answer:

 

E

 

Section:

 

 

3.5

 

40)

 

How is (CH3)3CCHClCH3 classified?

 

  1. A)

 

a primary alkyl halide

 

  1. B)

 

a primary alkyl chloride

 

  1. C)

 

a secondary alkyl chloride

 

  1. D)

 

a tertiary alkyl chloride

 

  1. E)

 

a quarternary alkyl chloride

 

Answer:

 

C

 

Section:

 

 

3.5

 

41)

 

How is NH4+Cl- classified?

 

  1. A)

 

a quarternary ammonium salt

 

  1. B)

 

a primary amine

 

  1. C)

 

a secondary amine

 

  1. D)

 

a secondary ammonium salt

 

  1. E)

 

a tertiary ammonium salt

 

Answer:

 

A

 

Section:

 

 

3.5

 

42)

 

How is the structure shown below classified?

 

 

 

  1. A)

 

a secondary alcohol

 

  1. B)

 

a primary alcohol

 

  1. C)

 

a quarternary alcohol

 

  1. D)

 

a tertiary alcohol

 

  1. E)

 

an ether

 

Answer:

 

A

 

Section:

 

 

3.5

 

43)

 

What is the hybridization of the nitrogen atom in CH3NH2?

 

  1. A)

 

sp

 

  1. B)

 

sp2

 

  1. C)

 

sp3

 

  1. D)

 

ssp3

 

  1. E)

 

a primary amine

 

Answer:

 

C

 

Section:

 

 

3.6

 

44)

 

What is the hybridization of the carbon atom in CH3NH2?

 

  1. A)

 

3sp3

 

  1. B)

 

sp

 

  1. C)

 

sp2

 

  1. D)

 

sp3

 

  1. E)

 

d2sp3

 

Answer:

 

D

 

Section:

 

 

3.6

 

45)

 

What is the hybridization of the oxygen atom in CH3CH2OH?

 

  1. A)

 

sp

 

  1. B)

 

4sp3

 

  1. C)

 

sp2

 

  1. D)

 

d2sp3

 

  1. E)

 

sp3

 

Answer:

 

E

 

Section:

 

 

3.6

 

46)

 

Which of the following statements is correct for a saturated alkyl halide?

 

  1. A)

 

the C-X bond results from overlap of the s orbital of carbon and the p orbital of the halogen (X)

 

  1. B)

 

the C-X bond results from overlap of the p orbital of carbon and the p orbital of the halogen (X)

 

  1. C)

 

the C-X bond results from overlap of the sp3 orbital of carbon and the p orbital of the halogen (X)

 

  1. D)

 

the C-X bond results from overlap of the sp2 orbital of carbon and the p orbital of the halogen (X)

 

  1. E)

 

the C-X bond results from overlap of the sp orbital of carbon and the p orbital of the halogen (X)

 

Answer:

 

C

 

Section:

 

 

3.6

 

47)

 

Where are the two lone pairs of electrons of the oxygen atom in an alcohol molecule located?

 

  1. A)

 

in two s orbitals

 

  1. B)

 

in two p orbitals

 

  1. C)

 

in two sp orbitals

 

  1. D)

 

in two sp2 orbitals

 

  1. E)

 

in two sp3 orbitals

 

Answer:

 

E

 

Section:

 

 

3.6

 

48)

 

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

 

Answer:

 

Chlorine is a larger atom than fluorine and uses a 3p rather than 2p orbital. The overlap of a carbon 2sp3 orbital with a chlorine 3p orbital is not as good as the overlap of a carbon 2sp3 orbital with a fluorine 2p orbital, causing the bond to be longer

and weaker.

 

Section:

 

 

3.6

 

49)

 

Explain why CH3CH2CH2CH2OH (74g/mol) has a boiling point of 117.3°C while CH3CH2CH2CH2CH3 (72g/mol) has a boiling point of 36.1°C.

 

Answer:

 

The alcohol has to overcome van der Waals forces, dipole-dipole interactions, and hydrogen bonding in order to reach the boiling point while the alkane of similar molar mass (molecular weight) only has van der Waals forces to overcome which are the weakest form of intermolecular interactions.

 

Section:

 

 

3.7

 

50)

 

What type of intermolecular interactions does (CH3CH2)2NH undergo?

 

  1. A)

 

induced dipole-induced dipole

 

  1. B)

 

dipole-dipole

 

  1. C)

 

hydrogen bonding

 

  1. D)

 

A and B

 

  1. E)

 

A, B, and C

 

Answer:

 

E

 

Section:

 

 

3.7

 

51)

 

Which of the following is the strongest interaction?

 

  1. A)

 

a covalent bond

 

  1. B)

 

induced dipole-induced dipole interactions

 

  1. C)

 

dipole-dipole interactions

 

  1. D)

 

hydrogen bonding

 

  1. E)

 

van der Waals

 

Answer:

 

A

 

Section:

 

 

3.7

 

52)

 

Rank the following molecules in increasing order of solubility in water: HOCH2CH2OH, CH3CH2OH, CH3CH2CH3

 

Answer:

 

CH3CH2CH3 < CH3CH2OH < HOCH2CH2OH

 

Section:

 

 

3.7

 

53)

 

Which of the following will have the lowest boiling point?

 

  1. A)

 

CH3Cl

 

  1. B)

 

CH4

 

  1. C)

 

CH2Cl2

 

  1. D)

 

CHCl3

 

  1. E)

 

CCl4

 

Answer:

 

B

 

Section:

 

 

3.7

 

54)

 

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

 

  1. A)

 

 

 

 

  1. B)

 

CH3CH2CH2CH3

 

  1. C)

 

 

 

 

  1. D)

 

CH3CH2CH2CH2CH3

 

  1. E)

 

 

 

 

Answer:

 

D

 

Section:

 

 

3.7

 

55)

 

Which of the following has the lowest boiling point?

 

  1. A)

 

CH3CH2CH2CH2CH2CH3

 

  1. B)

 

 

 

 

  1. C)

 

 

 

 

  1. D)

 

 

 

 

  1. E)

 

CH3CH2CH2CH2CH2CH2CH3

 

Answer:

 

C

 

Section:

 

 

3.7

 

56)

 

Which of the following has the greatest solubility in CH3CH2CH2CH3?

 

  1. A)

 

CH3OH

 

  1. B)

 

CH3O-Na+

 

  1. C)

 

CH3NH2

 

  1. D)

 

CH3OCH3

 

  1. E)

 

(CH3)3CH

 

Answer:

 

E

 

Section:

 

 

3.7

 

57)

 

Which of the following is the most soluble in H2O?

 

  1. A)

 

CH3OCH3

 

  1. B)

 

CH3CH2OH

 

  1. C)

 

CH3CH2Cl

 

  1. D)

 

CH3CH2CH3

 

  1. E)

 

CH3CHO

 

Answer:

 

B

 

Section:

 

 

3.7

 

58)

 

Which of the following would have the highest boiling point?

 

  1. A)

 

CH3CH2OCH2CH2OCH3

 

  1. B)

 

CH3OCH2CH2CH2OCH3

 

  1. C)

 

HOCH2CH2CH2CH2OH

 

  1. D)

 

CH3CH2OCH2OCH2CH3

 

  1. E)

 

 

 

 

Answer:

 

C

 

Section:

 

 

3.7

 

59)

 

Explain why has a lower boiling point than CH3CH2CH2CH3.

 

Answer:

 

CH3CH2CH2CH3 has greater dispersion forces because it has an extended structure and has a greater contact area than isobutane. Therefore, the boiling point of CH3CH2CH2CH3 is higher.

 

Section:

 

 

3.7

 

60)

 

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

 

Answer:

 

The nitrogen in a tertiary amine is not attached to a hydrogen. Recall that for a molecule to exhibit hydrogen bonding, it must have a hydrogen attached to a highly electronegative atom such as F, N, or O.

 

Section:

 

 

3.7

 

61)

 

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

 

Answer:

 

Since hydrogen bonding is possible for propylamine and not for trimethylamine, the boiling point is higher for propylamine.

 

Section:

 

 

3.7

 

62)

 

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

 

CH3CH2CH2OH      or    CH3CH2OCH3

 

Answer:

 

CH3CH2CH2OH has the higher boiling point since it is capable of intermolecular hydrogen bonding.

 

Section:

 

 

3.7

 

63)

 

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

 

Answer:

 

One would not expect NaCl to be highly soluble in hexane. NaCl is an ionic solid (i.e., a very polar material) while hexane is nonpolar. Nonpolar solvent molecules do not solvate ions well. The attractions of oppositely charged ions to each other are vastly greater than the extremely weak attractions of the ions for the solvent.

 

Section:

 

 

3.7

 

64)

 

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

 

CH3OCH3     or      CH3CH2OH

 

Answer:

 

CH3CH2OH is more soluble in water since it can donate a hydrogen bond to water and accept a hydrogen bond from water. CH3OCH3 can only accept a hydrogen bond from water; it has no acidic hydrogen which can hydrogen bond to water.

 

Section:

 

 

3.7

 

65)

 

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

 

(CH3)2NH      or     CH3CH2CH3

 

Answer:

 

(CH3)2NH is more soluble in water since it can hydrogen bond with water. Alkanes are not capable of hydrogen bonding with water.

 

Section:

 

 

3.7

 

66)

 

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

 

Answer:

 

Van der Waal’s or London forces

 

Section:

 

 

3.7

 

67)

 

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?

 

  1. A)

 

2,3-dimethylbutane < 2-methylpentane < n-hexane

 

  1. B)

 

2-methylpentane < n-hexane < 2,3-dimethylbutane

 

  1. C)

 

2-methylpentane < 2, 3-dimethylbutane < n-hexane

 

  1. D)

 

n-hexane < 2-methylpentane < 2,3-dimethylbutane

 

  1. E)

 

n-hexane < 2,3-dimethylbutane < 2-methylpentane

 

Answer:

 

A

 

Section:

 

 

3.7

 

68)

 

What is the strongest intermolecular force present in liquid ethanol?

 

  1. A)

 

induced dipole-induced dipole

 

  1. B)

 

dipole-dipole, specifically hydrogen bonding

 

  1. C)

 

dipole-dipole, but not hydrogen bonding

 

  1. D)

 

ion-dipole

 

  1. E)

 

ion-ion

 

Answer:

 

B

 

Section:

 

 

3.7

 

69)

 

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

 

  1. A)

 

a tertiary amine

 

  1. B)

 

a quaternary ammonium salt

 

  1. C)

 

an alcohol

 

  1. D)

 

an ether

 

  1. E)

 

an alkyl chloride

 

Answer:

 

B

 

Section:

 

 

3.7

 

70)

 

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

 

Answer:

 

(CH3)2CHN(CH3)2 < (CH3)2CHCH2NHCH3 < (CH3)2CHCH2CH2NH2

 

Section:

 

 

3.7

 

71)

 

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

 

  1. A)

 

molecular formula

 

  1. B)

 

configuration

 

  1. C)

 

conformation

 

  1. D)

 

constitution

 

  1. E)

 

structure

 

Answer:

 

C

 

Section:

 

 

3.8

 

72)

 

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

 

 

 

  1. A)

 

I

 

  1. B)

 

II

 

  1. C)

 

III

 

  1. D)

 

IV

 

  1. E)

 

V

 

Answer:

 

A

 

Section:

 

 

3.8

 

73)

 

Draw the Newman structure for the most stable conformation of 1-bromopropane considering rotation about the C1-C2 bond.

 

Answer:

 

 

 

 

Section:

 

 

3.8

 

74)

 

Draw a Newman projection of the most stable conformation of 2-methylpropane as viewed along the C1-C2 bond axis.

 

Answer:

 

 

 

 

Section:

 

 

3.8

 

75)

 

Explain why a staggered conformation has a low energy than an eclipsed conformation.

 

Section:

 

 

3.8

 

76)

 

Define the term “conformation.”

 

Answer:

 

Conformations are different arrangements of the same molecule formed by rotations about single bonds.

 

Section:

 

 

3.8

 

77)

 

View a butane molecule along the C2-C3 bond and provide a Newman projection of the lowest energy conformer.

 

Answer:

 

 

 

 

Section:

 

 

3.8

 

78)

 

Which of the following best explains the relative stabilities of the eclipsed and staggered forms of ethane? The __________ form has the most __________ strain.

 

  1. A)

 

eclipsed; steric

 

  1. B)

 

eclipsed; torsional

 

  1. C)

 

staggered; steric

 

  1. D)

 

staggered; torsional

 

Answer:

 

B

 

Section:

 

 

3.8

 

79)

 

Draw the Newman projection of the most stable conformation that results due to rotation about the C2-C3 bond in 2,3-dimethylbutane.

 

Answer:

 

 

 

 

Section:

 

 

3.8

 

80)

 

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

 

  1. A)

 

cyclopropane < cyclobutane < cyclohexane < cycloheptane

 

  1. B)

 

cyclohexane < cyclopentane < cyclobutane < cyclopropane

 

  1. C)

 

cyclopentane < cyclobutane < cyclopentane < cyclopropane

 

  1. D)

 

cyclopentane < cyclopropane < cyclobutane < cyclohexane

 

  1. E)

 

cyclopropane < cyclopentane < cyclobutane < cyclohexane

 

Answer:

 

B

 

Section:

 

 

3.9

 

81)

 

Describe the source of angle strain and torsional strain present in cyclopropane.

 

Answer:

 

The angle strain arises from the compression of the ideal tetrahedral bond angle of 109.5° to 60°. The large torsional strain occurs since all C-H bonds on adjacent carbons are eclipsed.

 

Section:

 

 

3.9

 

82)

 

What is Latin for “across”?

 

  1. A)

 

substituent

 

  1. B)

 

cis

 

  1. C)

 

trans

 

  1. D)

 

geometric isomer

 

Answer:

 

C

 

Section:

 

 

3.11

 

83)

 

Which of the following describes the most stable conformation of trans-1-tert-butyl-3-methylcyclohexane?

 

  1. A)

 

Both groups are equatorial.

 

  1. B)

 

Both groups are axial.

 

  1. C)

 

The tert-butyl group is equatorial.

 

  1. D)

 

The tert-butyl group is axial and the methyl group is equatorial.

 

  1. E)

 

none of the above

 

Answer:

 

C

 

Section:

 

 

3.12

 

84)

 

Draw the most stable conformation of cis-1-isopropyl-2-methylcyclohexane.

 

Answer:

 

 

 

 

Section:

 

 

3.12

 

85)

 

Which of the following has two equatorial alkyl substituents in its most stable conformation?

 

  1. A)

 

1,1-dimethylcyclohexane

 

  1. B)

 

cis-1,2-dimethylcyclohexane

 

  1. C)

 

cis-1,3-diethylcyclohexane

 

  1. D)

 

cis-1,4-diethylcyclohexane

 

  1. E)

 

all of the above

 

Answer:

 

C

 

Section:

 

 

3.12

 

86)

 

Draw the most stable conformation of trans-decalin.

 

Answer:

 

 

 

 

Section:

 

 

3.13