WorksheetsCHEM 241 Chapter 6 - Alkenes - NSU
Total questions: 82
Worksheet time: 2hrs 35mins
Which of the following hydrocarbons contains at least one double bond?
Alkanes
Alkenes
Alkynes
What is the correct structure for 2 - butene?
Name the following molecule?
2,3-dichlorobutene
cis-2,3-dichlorobutene
trans-2,3-dichlorobutene
Name the compound
nonene
2,2-dimethyl-3-heptene
1,1,5-trimethyl-2-hexene
2,6-dimethyl-3-heptene
Name the polymer formed from this monomer
chloroethene
chloroethane
dichloroethene
dichloroethane
CH3CH2CH2CH=CHCH2CH3. What is the IUPAC name for the compound?
2-Butene
3-Heptene
2-Methyl-2-Pentene
What is the expected product?
What is the expected product?
Choose conditions to synthesize the product.
Which conditions produce an aldehyde?
Which conditions proceed with anti addition across the alkene pi bond?
H2, Pd/C
OsO4, H2O2
1. BH3-THF
2. NaOH, H2O2
Br2, H2O
Which conditions follow Markovnikov's rule?
H2, Pd/C
KMnO4, NaOH, cold
1. BH3-THF
2. NaOH, H2O2
HCl
Under which conditions might you see evidence of carbocation rearrangement?
1. O3, −78 °C
2. CH3SCH3
1. BH3-THF
2. H2O2, NaOH
HBr
1. Hg(OAc)2, H2O
2. NaBH4
Which is the expected product?
What is the major product if HBr is added to the alkene shown?
What (major) carbocation intermediate will be formed here?
What is the expected major product if HBr is added to the alkene shown?
Which of the carbocations shown is likely to rearrange?
(Choose ALL)
What reagent(s) are needed to achieve the transformation shown?
H+/H2O
H+/H2O2
H2O
1. BH3/THF
2. OH-/H2O2
What is the major product if HBr is added to the alkene shown?
What (major) carbocation intermediate will be formed here?
What is the expected major product if HBr is added to the alkene shown?
Which of the carbocations shown is likely to rearrange?
(Choose ALL)
What is the expected major product of the reaction shown? (Hint: Draw this reaction!)
What reagent(s) are needed to achieve the transformation shown?
H+/H2O
H+/H2O2
H2O
1. BH3·THF
2. OH-/H2O2
What is the major product for the following reaction?
What reaction is this?
Halgenation
Halohydrin Formation
Hydrohalogenation
Hydroboration
What is Alkene Reaction
Halogenation
Halohydrin
Hydrohalogenation
Catalytic Hydrogenation
What reaction is presented?
Halogenation
Halohydrin
Hydroboration
Catalytic Hydrogenation
Name the alkene reaction
Halogenation
Halohydrin
Hydrohalogenation
Hydroboration-Oxidation
Name the reaction
Hydrohalogentation
Anti Dihydroxylation
Halohydrin Formation
Acid-Catalyzed Hydration
Catalytic Hyrdogenation
Name the alkene reaction
Hydrogenation
Catalytic Hydrogenation
Acid-Catalyzed Hydration
Anti Dihydroxylation
Name the reaction
Halohydrin Formation
Dihydroxylation
Acid-Catalyzed Hydration
Catalytic Hydrogenation
Identify the relevant information for a hydrohalogenation reaction:
arrow pushing patterns (in order): (a) and (b)
stereoselectivity: (c)
regioselectivity: (d)
Identify the relevant information for a hydrohalogenation reaction involving peroxides:
stereoselectivity: (a)
regioselectivity: (b)
Hydrohalogenation Reaction
Regioselectivity:
The Hydrogen Takes Up the LESS Substituted Carbon
Follows Markovnikov's
The Halogen Takes Up the MORE Substituted Carbon
The Hydrogen Takes Up the MORE Substituted Carbon
The Halogen Takes Up the LESS Substituted Carbon
The Regioselectivity of an Ionic Addition Reaction is Determined By What?
The Preference for the reaction to proceed through the more stable intermediate
The Preference for the reaction based off of charge
The Preference for the reaction for less steric hindrance
The Preference for the reaction to process through the less stable intermediate
Alkene Reactions Which Are Addition Reactions
Hydrohalgenation
Acid Catalyzed
Hydroboration-Oxidation
Anti Dihydroxyl
Catalytic Hydrogenation
Hydrohalogenation Undergoes
Proton Transfer
Proton Transfer x2
Nucleophillic ATTACK!
Loss of Leaving Group ;,(
Rearrangement
In Hydrohalogenation The pi Bond Acts As a _____
While the Hydrogen Acts as a ____
-Nucleophile
-Electrophile
-Nucleophile
-Nucleophile
-Electrophile
-Electrophile
-Electrophile
-Nucleophile
Hydroboration-Oxidation Reaction
______ Addition of ______
-Anti-Markovnikov's
-Water
-Markovnikov's
-Water
-Anti-Markovnikov's
-Water across a pi bond
-Markonikov's
-Water across a pi bond
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.
What two reactions achieve Markovnikov's addition of water across a pi bond
Acid-catalyzed Hydration
Oxymercuration-Demercuration
Hydroboration-Oxidation
Catalytic Hydrogenation
The boron atom in Hydroboration-Oxidation is (a) an (b) octet.
Identify the reagents for hydroboration-oxidation:
solvent: (a)
electrophile(s): (b) and (c)
nucleophile(s): (d) and (e)
Hydroboration-Oxidation has a _____ process
Concerted
Stepwise
Practical
One Step
Hydroboration-Oxidation
The OH is installed in the (a) substituted position
Is this isomer E or Z?
Z
E
Name the following compound
1Z,3Z-1,3-butandiene
1Z,3E-1,3-butandiene
1E,3E-1,3-butandiene
1E,3Z-1,3-butandiene
What reaction is this?
Halgenation
Halohydrin Formation
Hydrohalogenation
Hydroboration
What is Alkene Reaction
Halogenation
Halohydrin
Hydrohalogenation
Catalytic Hydrogenation
What reaction is presented?
Halogenation
Halohydrin
Hydroboration
Catalytic Hydrogenation
Name the alkene reaction
Halogenation
Halohydrin
Hydrohalogenation
Hydroboration-Oxidation
Name the reaction
Halohydrin Formation
Dihydroxylation
Acid-Catalyzed Hydration
Catalytic Hydrogenation
Hydrohalogenation Reaction
Treat alkenes with ___ and a(n) _______ reaction
-Base
-Addition
-Halogen & Hydrogen
-Addition
-Two Hydrogens in Metal Solvent
-Addition
-Two Halogens
-Addition
The regioselectivity of a polar reaction is determined ____.
The preference for the reaction to proceed through the more stable intermediate
The Preference for the reaction based off of charge
The Preference for the reaction for less steric hindrance
The Preference for the reaction to process through the less stable intermediate
Hydrohalogenation Undergoes
Proton Transfer
Proton Transfer x2
Nucleophilic attack
Loss of Leaving Group
Rearrangement
In Hydrohalogenation The pi Bond Acts As a _____
While the Hydrogen Acts as a ____
-Nucleophile
-Electrophile
-Nucleophile
-Nucleophile
-Electrophile
-Electrophile
-Electrophile
-Nucleophile
Hydroboration-Oxidation Reaction
______ Addition of ______
-Anti-Markovnikov's
-Water
-Markovnikov's
-Water
-Anti-Markovnikov's
-Water across a pi bond
-Markonikov's
-Water across a pi bond
Hydroboration-Oxidation Reaction
Installs the ____ Group at the ____ substituted Position
-OH
-Less
-BH3
-Less
-OH
-More
-BH3
-More
Hydroboration-Oxidation
Solvent is:
Because it can:
-THF
-Donate Electron Density into the empty p orbital of Boron
-THF
-Increase the concentration at equilibrium
-Water
-Protic Polar substance to Promote Hydrogen Bonding
-Water
-Donate Electron Density From the Oxygen
Hydroboration-Oxidation Has a _____ Process
Concerted
Stepwise
Practical
One Step
Hydroboration is repeated until all BH3 turns into BR3
True
False
What is the expected product?
What is the expected product?
Choose conditions to synthesize the product.
Which conditions produce an aldehyde?
Which conditions proceed with anti addition across the alkene pi bond?
H2, Pd/C
OsO4, H2O2
1. BH3-THF
2. NaOH, H2O2
Br2, H2O
Which conditions follow Markovnikov's rule?
H2, Pd/C
KMnO4, NaOH, cold
1. BH3-THF
2. NaOH, H2O2
HCl
What are the reagents required for the following reaction?
H2O, NaOH
H2O, H2SO4
Which one is the Markovnikov's Product of the HBr addition to the following compound?
What is the structure of A?
What are the reagents required for the following reaction?
H2O, NaOH
H2O, H2SO4
Which one is the Markovnikov's Product of the HBr addition to the following compound?
What is the product of the Br2 addition to methycyclohexene?
1,2-dibromo-1-methylcyclohexene
1,2-dibromo-1-methylcyclohexane
What is the structure of A?
What are the reagents required for the following transformation?
KMnO4
H2O, H2SO4
What is the structure of A?
Which one cannot be the structure of A?
2-butene
2-butyne
1-butyne
Identify the reagents that would provide the following products
1) Hg(OAc)2, H20, 2) NaBH4
KMnO4, NaOH, cold
HCl
H2, Ni
Br2, H2O
Identify which method would provide the most efficient synthesis for this transformation
1) HBr, 2) NaOMe
1) H20, 2) NaOtBu
1) Hg(OAc)2, NaOH, 2)NaBH4, 3) NaOEt
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.
What are the names of the different products obtained when Compound A reacts with sodium ethoxide and tBuOK?
What is the molecular formula for compound A?
What type of reactions were performed?
