Essential Organic Chemistry (Bruice)

Chapter 4

Essential Organic Chemistry (Bruice)

Chapter 4 Alkenes: Structure, Nomenclature, Stability, and an Introduction to Reactivity

1)

What is the molecular formula of the hydrocarbon that contains 5 carbon atoms, one ring, and one π bond?
Answer:

C5H8
Section: 4.1

2)

What is the molecular formula of the hydrocarbon that contains 8 carbon atoms, one ring, and two π bonds?
Answer:

C8H12
Section: 4.1

3)

What is the condensed formula of an unsaturated hydrocarbon containing three carbons?

Answer:

CH2=CHCH3
Section: 4.1

4)

What is the common name for the following compound?

A)

t-Butylene
B)

sec-Butylene
C)

Isobutylene
 Essential Organic Chemistry (Bruice)
Chapter 4

D)

Butylene
E)

Methylpropylene
Answer:

C
Section: 4.2

5)

What is the IUPAC name for the following compound?

A)

2-methyl-1-butene
B)

Isopentene
C)

2-methylbutene
D)

2-Ethylpropene
E)

3-methyl-3-butene
Answer:

A
Section: 4.2
 Essential Organic Chemistry (Bruice)
Chapter 4

6)

What is the IUPAC name for the following compound?

A)

5-methylcyclohexene
B)

4-methylcyclohexene
C)

1-methyl-3-cyclohexene
D)

1-methyl-4-cyclohexene
E)

methylcyclohexene
Answer:

B
Section: 4.2

7)

Which of the following is vinyl chloride?

A)

CH3CH2Cl
B)

CH2CHCH2Cl
C)

CH2CHCl
D)
 Essential Organic Chemistry (Bruice)
Chapter 4

E)

Answer:

C
Section: 4.2

8)

Provide the proper IUPAC name for the alkene shown below.

Answer:

6-bromo-1-methylcyclohexene
Section: 4.2

9)

Provide the systematic name of the alkene below.

Answer:

2-ethyl-1-hexene
Section: 4.2
 Essential Organic Chemistry (Bruice)
Chapter 4

10)

Which of the following is an allylic alcohol?

A)

CH2=CHCH2OCH3
B)

CH2=CHCH2CH3
C)

HOCH=CHCH2CH3
D)

CH3CH=CHCH2OH
E)

CH2=CHCH2CH2OH
Answer:

D
Section: 4.2

11)

Provide the systematic name of the compound below.

Answer:

5-isobutyl-1-methylcyclopentene
Section: 4.2

12)

Which of the following statements about ethene, C2H4, is incorrect?

A)
 Essential Organic Chemistry (Bruice)
Chapter 4

The H-C-H bond angles are approximately 109.5°.

B)

All of the hydrogen atoms are in the same plane.

C)

There is a total of five sigma bonds.

D)

The carbon atoms are sp2 hybridized.

E)

The H-C-H bond angles are approximately 120°.

Answer:

A
Section: 4.3

13)

Which of the following statements about propene, CH3CHCH2, is correct?

A)

All nine atoms lie in the same plane.

B)

The compound has a cis and trans isomer.

C)

It generally acts as a Lewis acid.

D)

There is a total of eight sigma bonds.

E)

All the carbon atoms are sp2 hybridized.

Answer:

D
Section: 4.3

14)

Which of the following is capable of exhibiting cis-trans isomerism?

A)
 Essential Organic Chemistry (Bruice)
Chapter 4

1-butene
B)

1-pentene
C)

cyclohexene
D)

ethene
E)

2-butene
Answer:

E
Section: 4.4

15)

Draw all the possible constitutional isomers of C4H8.

Answer:

Section: 4.4

16)

What is the IUPAC name of

A)

cis-4-methyl-2-pentene
B)

cis-2-methyl-3-pentene
C)
 Essential Organic Chemistry (Bruice)
Chapter 4

trans-2-methyl-3-pentene
D)

(E)-2-methyl-3-pentene
E)

trans-4-methyl-2-pentene
Answer:

E
Section: 4.4

17)

What is the IUPAC name of

A)

1-chloro-2-pentene
B)

trans-4-chloro-3-butene
C)

cis-1-chloro-1-butene
D)

(Z)-1-chloro-2-butene
E)

trans-1-chloro-1-propene
Answer:

C
Section: 4.4
 Essential Organic Chemistry (Bruice)
Chapter 4

18)

Assign the E or Z configuration to the following molecule:

Answer:

The molecule has a Z configuration based on the priority rule established by Cahn-Ingold-Prelog.

Section: 4.5

19)

Provide the proper IUPAC name for the alkene shown below.

Answer:

(E)-3,4-dimethyl-3-heptene
Section: 4.5

20)

Which of the following best describes the geometry about the carbon-carbon double bond in the alkene below?

A)

E
 Essential Organic Chemistry (Bruice)
Chapter 4

B)

Z
C)

neither E nor Z
D)

cis
E)

trans
Answer:

C
Section: 4.5
 Essential Organic Chemistry (Bruice)
Chapter 4

21)

Draw the structure of (Z)-4-ethyl-3-methyl-3-heptene.

Answer:

Section: 4.5

22)

Draw and name the six alkenes which have the molecular formula C5H10.
Answer:

Section: 4.4 and 4.5

 Essential Organic Chemistry (Bruice)
Chapter 4

23)

Which of the following is the most stable alkene?

A)

B)

C)

D)

E)

Answer:

E
Section: 4.6

24)

Which of the following is the most stable alkene?

A)

trans-3-hexene
 Essential Organic Chemistry (Bruice)
Chapter 4

B)

cis-3-hexene
C)

1-hexene
D)

cis-2,2,5,5-tetramethyl-3-hexene
E)

(Z)-3-hexene
Answer:

A
Section: 4.6

25)

Which of the following is not an electrophile?

A)

H+
B)

BF3
C)

+NO2
D)

Fe+3
E)

CH2CH2
Answer:

E
Section: 4.7
 Essential Organic Chemistry (Bruice)
Chapter 4

26)

Which of the following is not a nucleophile?

A)

FeBr3
B)

Br-
C)

NH3
D)

E)

CH3OCH3
Answer:

A
Section: 4.7

27)

Draw the curved arrows to show how CH3CH=CHCH3 reacts with HBr to form a
carbocation.
Answer:

Section: 4.7

28)

A nucleophile acts as a ________ when it reacts with an electrophile.

A)

Bronsted-Lowry acid
B)

Arrhenius base
 Essential Organic Chemistry (Bruice)
Chapter 4

C)

Lewis acid
D)

Lewis base
E)

none of the above

Answer:

D
Section: 4.7

29)

Which of the following is correct?

A)

Curved arrows are always drawn from an electron poor center to an electron rich center.
B)

A doubled headed arrow means one electron has been moved.

C)

Curved arrows are always drawn from an electron rich center to an electron poor center.
D)

A single headed arrow means two electrons have been moved.

E)

Curved arrows are used to show movement of protons.

Answer:

C
Section: 4.7
 Essential Organic Chemistry (Bruice)
Chapter 4

30)

How many transition states are present in the following reaction diagram?

A)

3
B)

4
C)

5
D)

2
E)

1
Answer:

D
Section: 4.8

31)

What is used to represent a transition state structure?

A)

The structure is inside parentheses which have a double dagger superscript.

B)

The structure is inside brackets which have a single dagger superscript.

C)

The structure is inside brackets which have a double dagger superscript.

D)

The structure is inside brackets which have a triple dagger superscript.

 Essential Organic Chemistry (Bruice)
Chapter 4

E)

The structure is inside parentheses which have a single dagger superscript.

Answer:

C
Section: 4.8

32)

An increase in which of the following results in a decrease in the rate of the chemical reaction?
A)

temperature
B)

concentration
C)

collision frequency
D)

energy of activation
E)

fraction of collisions with proper orientation

Answer:

D
Section: 4.8

33)

An increase in which of the following will occur if the reaction temperature is increased?

I. Energy of activation
II. Collision frequency
III. Fraction of collisions with sufficient energy
A)

I and II
B)

I and III
C)
 Essential Organic Chemistry (Bruice)
Chapter 4

II and III
D)

I, II, and III

E)

I
Answer:

C
Section: 4.8
 Essential Organic Chemistry (Bruice)
Chapter 4

34)

What is the activation energy for the reaction in the following diagram?

A)

A
B)

B
C)

C
D)

D
E)

E
Answer:

E
Section: 4.8

35)

Which of the following correctly describes intermediates and/or transition states?

A)

Transition states occur at minima on reaction coordinate diagrams.

B)

Both transition states and intermediates occur at maxima on reaction coordinate diagrams.
C)

An intermediate is always produced after the rate-determining step of a reaction mechanism.

D)

Transition states have partially formed bonds whereas intermediates have fully formed bonds.
 Essential Organic Chemistry (Bruice)
Chapter 4

E)

none of the above

Answer:

D
Section: 4.8

36)

Based on the following energy diagram, what is B?

A)

activation energy
B)

activated complex
C)

transition state
D)

intermediate
E)

none of the above

Answer:

D
Section: 4.8
 Essential Organic Chemistry (Bruice)
Chapter 4

37)

The reaction step that has its transition state at the highest point on the reaction coordinate is the called the __________.
A)

rate-determining step
B)

activation energy
C)

transition step
D)

product favored step

E)

reactant favored step

Answer:

A
Section: 4.8