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CHEM 241 Chapter 6 - Alkenes - NSU

Total questions: 82

Worksheet time: 2hrs 35mins

Name
Class
Date
1.

Which of the following hydrocarbons contains at least one double bond?

a)

Alkanes

b)

Alkenes

c)

Alkynes

2.

What is the correct structure for 2 - butene?

a)
b)
c)
d)
3.

Name the following molecule?

a)

2,3-dichlorobutene

b)

cis-2,3-dichlorobutene

c)

trans-2,3-dichlorobutene

4.

Name the compound

a)

nonene

b)

2,2-dimethyl-3-heptene

c)

1,1,5-trimethyl-2-hexene

d)

2,6-dimethyl-3-heptene

5.

Name the polymer formed from this monomer

a)

chloroethene

b)

chloroethane

c)

dichloroethene

d)

dichloroethane

6.

CH3CH2CH2CH=CHCH2CH3. What is the IUPAC name for the compound?

a)

2-Butene

b)

3-Heptene

c)

2-Methyl-2-Pentene

7.

What is the expected product?

a)
b)
c)
d)
8.

What is the expected product?

a)
b)
c)
d)
9.

Choose conditions to synthesize the product.

a)
b)
c)
d)
10.

Which conditions produce an aldehyde?

a)
b)
c)
d)
11.

Which conditions proceed with anti addition across the alkene pi bond?

a)

H2, Pd/C

b)

OsO4, H2O2

c)

1. BH3-THF

2. NaOH, H2O2

d)

Br2, H2O

12.

Which conditions follow Markovnikov's rule?

a)

H2, Pd/C

b)

KMnO4, NaOH, cold

c)

1. BH3-THF

2. NaOH, H2O2

d)

HCl

13.

Under which conditions might you see evidence of carbocation rearrangement?

a)

1. O3, −78 °C-78\ \degree C  

2. CH3SCH3

b)

1. BH3-THF

2. H2O2, NaOH

c)

HBr

d)

1. Hg(OAc)2, H2O

2. NaBH4

14.

Which is the expected product?

a)
b)
c)
d)
15.

What is the major product if HBr is added to the alkene shown?

a)
b)
c)
d)
e)
16.

What (major) carbocation intermediate will be formed here?

a)
b)
c)
d)
e)
17.

What is the expected major product if HBr is added to the alkene shown?

a)

b)

c)

d)

e)

18.

Which of the carbocations shown is likely to rearrange?

(Choose ALL)

a)
b)
c)
19.

What reagent(s) are needed to achieve the transformation shown?

a)

H+/H2O

b)

H+/H2O2

c)

H2O

d)

1. BH3/THF

2. OH-/H2O2

20.

What is the major product if HBr is added to the alkene shown?

a)
b)
c)
d)
e)
21.

What (major) carbocation intermediate will be formed here?

a)
b)
c)
d)
e)
22.

What is the expected major product if HBr is added to the alkene shown?

a)

b)

c)

d)

e)

23.

Which of the carbocations shown is likely to rearrange?

(Choose ALL)

a)
b)
c)
24.

What is the expected major product of the reaction shown? (Hint: Draw this reaction!)

a)
b)
c)
25.

What reagent(s) are needed to achieve the transformation shown?

a)

H+/H2O

b)

H+/H2O2

c)

H2O

d)

1. BH3·THF

2. OH-/H2O2

26.

What is the major product for the following reaction?

a)
b)
c)
d)
e)
27.

What reaction is this?

a)

Halgenation

b)

Halohydrin Formation

c)

Hydrohalogenation

d)

Hydroboration

28.

What is Alkene Reaction

a)

Halogenation

b)

Halohydrin

c)

Hydrohalogenation

d)

Catalytic Hydrogenation

29.

What reaction is presented?

a)

Halogenation

b)

Halohydrin

c)

Hydroboration

d)

Catalytic Hydrogenation

30.

Name the alkene reaction

a)

Halogenation

b)

Halohydrin

c)

Hydrohalogenation

d)

Hydroboration-Oxidation

31.

Name the reaction

a)

Hydrohalogentation

b)

Anti Dihydroxylation

c)

Halohydrin Formation

d)

Acid-Catalyzed Hydration

e)

Catalytic Hyrdogenation

32.

Name the alkene reaction

a)

Hydrogenation

b)

Catalytic Hydrogenation

c)

Acid-Catalyzed Hydration

d)

Anti Dihydroxylation

33.

Name the reaction

a)

Halohydrin Formation

b)

Dihydroxylation

c)

Acid-Catalyzed Hydration

d)

Catalytic Hydrogenation

34.

Identify the relevant information for a hydrohalogenation reaction:

arrow pushing patterns (in order): ​ (a)   and ​ (b)  

stereoselectivity: ​ (c)  

regioselectivity: ​ (d)  

Choose from the below words
PT
NA
racemic
markovnikov
SN1
SN2
anti-Markovnikov
syn-Markovnikov
nonpolar
35.

Identify the relevant information for a hydrohalogenation reaction involving peroxides:

stereoselectivity: ​ (a)  

regioselectivity: ​ (b)  

Choose from the below words
racemic
anti-markovnikov
syn-markovnikov
meso
achiral
cis
36.

Hydrohalogenation Reaction

Regioselectivity:

a)

The Hydrogen Takes Up the LESS Substituted Carbon

b)

Follows Markovnikov's

c)

The Halogen Takes Up the MORE Substituted Carbon

d)

The Hydrogen Takes Up the MORE Substituted Carbon

e)

The Halogen Takes Up the LESS Substituted Carbon

37.

The Regioselectivity of an Ionic Addition Reaction is Determined By What?

a)

The Preference for the reaction to proceed through the more stable intermediate

b)

The Preference for the reaction based off of charge

c)

The Preference for the reaction for less steric hindrance

d)

The Preference for the reaction to process through the less stable intermediate

38.

Alkene Reactions Which Are Addition Reactions

a)

Hydrohalgenation

b)

Acid Catalyzed

c)

Hydroboration-Oxidation

d)

Anti Dihydroxyl

e)

Catalytic Hydrogenation

39.

Hydrohalogenation Undergoes

a)

Proton Transfer

b)

Proton Transfer x2

c)

Nucleophillic ATTACK!

d)

Loss of Leaving Group ;,(

e)

Rearrangement

40.

In Hydrohalogenation The pi Bond Acts As a _____

While the Hydrogen Acts as a ____

a)

-Nucleophile

-Electrophile

b)

-Nucleophile

-Nucleophile

c)

-Electrophile

-Electrophile

d)

-Electrophile

-Nucleophile

41.

Hydroboration-Oxidation Reaction

______ Addition of ______

a)

-Anti-Markovnikov's

-Water

b)

-Markovnikov's

-Water

c)

-Anti-Markovnikov's

-Water across a pi bond

d)

-Markonikov's

-Water across a pi bond

42.

Provide the answers to the following questions about hydroboration oxidation:

Stereoselectivity: ​ (a)  

Regioselectivity: ​ (b)   which means that the nucleophile adds to the ​ (c)   substituted carbon and the electrophile adds to the ​ (d)   substituted carbon.

Choose from the below words
racemic
Anti-Markovnikov
less
more
meso
Markovnikov
equal
none
random
43.

What two reactions achieve Markovnikov's addition of water across a pi bond

a)

Acid-catalyzed Hydration

b)

Oxymercuration-Demercuration

c)

Hydroboration-Oxidation

d)

Catalytic Hydrogenation

44.

The boron atom in Hydroboration-Oxidation is ​ (a)   an ​ ​ (b)   octet.

Choose from the below words
electrophilic
unfilled
nucleophilic
filled
half
45.

Identify the reagents for hydroboration-oxidation:

solvent: ​ ​ (a)  

electrophile(s): ​ ​ (b)   and ​ (c)  

nucleophile(s): ​ (d)   and​ ​ (e)  

Choose from the below words
THF
DMF
DMSO
boron
H2O
OH
B(OH)3
Br-Br
H
pi bond
46.

Hydroboration-Oxidation has a _____ process

a)

Concerted

b)

Stepwise

c)

Practical

d)

One Step

47.

Hydroboration-Oxidation

The OH is installed in the (a)   substituted position

48.

Is this isomer E or Z?

a)

Z

b)

E

49.

Name the following compound

a)

1Z,3Z-1,3-butandiene

b)

1Z,3E-1,3-butandiene

c)

1E,3E-1,3-butandiene

d)

1E,3Z-1,3-butandiene

50.

What reaction is this?

a)

Halgenation

b)

Halohydrin Formation

c)

Hydrohalogenation

d)

Hydroboration

51.

What is Alkene Reaction

a)

Halogenation

b)

Halohydrin

c)

Hydrohalogenation

d)

Catalytic Hydrogenation

52.

What reaction is presented?

a)

Halogenation

b)

Halohydrin

c)

Hydroboration

d)

Catalytic Hydrogenation

53.

Name the alkene reaction

a)

Halogenation

b)

Halohydrin

c)

Hydrohalogenation

d)

Hydroboration-Oxidation

54.

Name the reaction

a)

Halohydrin Formation

b)

Dihydroxylation

c)

Acid-Catalyzed Hydration

d)

Catalytic Hydrogenation

55.

Hydrohalogenation Reaction

Treat alkenes with ___ and a(n) _______ reaction

a)

-Base

-Addition

b)

-Halogen & Hydrogen

-Addition

c)

-Two Hydrogens in Metal Solvent

-Addition

d)

-Two Halogens

-Addition

56.

The regioselectivity of a polar reaction is determined ____.

a)

The preference for the reaction to proceed through the more stable intermediate

b)

The Preference for the reaction based off of charge

c)

The Preference for the reaction for less steric hindrance

d)

The Preference for the reaction to process through the less stable intermediate

57.

Hydrohalogenation Undergoes

a)

Proton Transfer

b)

Proton Transfer x2

c)

Nucleophilic attack

d)

Loss of Leaving Group

e)

Rearrangement

58.

In Hydrohalogenation The pi Bond Acts As a _____

While the Hydrogen Acts as a ____

a)

-Nucleophile

-Electrophile

b)

-Nucleophile

-Nucleophile

c)

-Electrophile

-Electrophile

d)

-Electrophile

-Nucleophile

59.

Hydroboration-Oxidation Reaction

______ Addition of ______

a)

-Anti-Markovnikov's

-Water

b)

-Markovnikov's

-Water

c)

-Anti-Markovnikov's

-Water across a pi bond

d)

-Markonikov's

-Water across a pi bond

60.

Hydroboration-Oxidation Reaction

Installs the ____ Group at the ____ substituted Position

a)

-OH

-Less

b)

-BH3

-Less

c)

-OH

-More

d)

-BH3

-More

61.

Hydroboration-Oxidation

Solvent is:

Because it can:

a)

-THF

-Donate Electron Density into the empty p orbital of Boron

b)

-THF

-Increase the concentration at equilibrium

c)

-Water

-Protic Polar substance to Promote Hydrogen Bonding

d)

-Water

-Donate Electron Density From the Oxygen

62.

Hydroboration-Oxidation Has a _____ Process

a)

Concerted

b)

Stepwise

c)

Practical

d)

One Step

63.

Hydroboration is repeated until all BH3 turns into BR3

a)

True

b)

False

64.

What is the expected product?

a)
b)
c)
d)
65.

What is the expected product?

a)
b)
c)
d)
66.

Choose conditions to synthesize the product.

a)
b)
c)
d)
67.

Which conditions produce an aldehyde?

a)
b)
c)
d)
68.

Which conditions proceed with anti addition across the alkene pi bond?

a)

H2, Pd/C

b)

OsO4, H2O2

c)

1. BH3-THF

2. NaOH, H2O2

d)

Br2, H2O

69.

Which conditions follow Markovnikov's rule?

a)

H2, Pd/C

b)

KMnO4, NaOH, cold

c)

1. BH3-THF

2. NaOH, H2O2

d)

HCl

70.

What are the reagents required for the following reaction?

a)

H2O, NaOH

b)

H2O, H2SO4

71.

Which one is the Markovnikov's Product of the HBr addition to the following compound?

a)
b)
72.

What is the structure of A?

a)
b)
73.

What are the reagents required for the following reaction?

a)

H2O, NaOH

b)

H2O, H2SO4

74.

Which one is the Markovnikov's Product of the HBr addition to the following compound?

a)
b)
75.

What is the product of the Br2 addition to methycyclohexene?

a)

1,2-dibromo-1-methylcyclohexene

b)

1,2-dibromo-1-methylcyclohexane

76.

What is the structure of A?

a)
b)
77.

What are the reagents required for the following transformation?

a)

KMnO4

b)

H2O, H2SO4

78.

What is the structure of A?

a)
b)
79.

Which one cannot be the structure of A?

a)

2-butene

b)

2-butyne

c)

1-butyne

80.

Identify the reagents that would provide the following products

81.

Identify which method would provide the most efficient synthesis for this transformation

82-84.

A graduate student trying to synthesize a bromine containing starting compound (Compound A) which is not commercially available. However, their advisor is forcing them to prove they synthesized the compound correctly by reacting it with different reagents.

The student determined that compound A is achiral based on an experiment where it was subjected to plane polarized light. When compound A is reacted with sodium ethoxide it yields only one product (compound B). Using spectroscopy the student determined that the molecular formula of compound B would be C7H14. However, if compound A was treated with tBuOK instead it generated a different alkene, as determined by spectroscopy.

82.

What are the names of the different products obtained when Compound A reacts with sodium ethoxide and tBuOK?

4 lines
83.

What is the molecular formula for compound A?

4 lines
84.

What type of reactions were performed?

4 lines