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Questions and Answers
What suffix is commonly used in the nomenclature of alkenes?
What suffix is commonly used in the nomenclature of alkenes?
Electrophilic addition of H2O to alkenes is always anti-addition.
Electrophilic addition of H2O to alkenes is always anti-addition.
False
What is the regioselectivity when adding HBr to an alkene?
What is the regioselectivity when adding HBr to an alkene?
Markovnikov
In the bromination of alkenes, a ______ ion is formed as an intermediate.
In the bromination of alkenes, a ______ ion is formed as an intermediate.
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Match the reagents with their resulting products in electrophilic addition to alkenes:
Match the reagents with their resulting products in electrophilic addition to alkenes:
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Which reaction leads to syn addition?
Which reaction leads to syn addition?
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Electrophilic addition reactions can involve carbocation rearrangement.
Electrophilic addition reactions can involve carbocation rearrangement.
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What is the result of the hydroboration-oxidation reaction on an alkene?
What is the result of the hydroboration-oxidation reaction on an alkene?
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Using ______ as a reagent provides an anti addition mechanism.
Using ______ as a reagent provides an anti addition mechanism.
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Match the reagent with its type of selectivity:
Match the reagent with its type of selectivity:
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What is the condition required for oxidative cleavage of alkenes using ozonolysis?
What is the condition required for oxidative cleavage of alkenes using ozonolysis?
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Anti-Markovnikov addition occurs with the presence of a radical initiator.
Anti-Markovnikov addition occurs with the presence of a radical initiator.
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What is the product formation for syn addition using RCO3H (MCPBA)?
What is the product formation for syn addition using RCO3H (MCPBA)?
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Under reducing conditions, the products formed from oxidative cleavage yield ___ chiral centers.
Under reducing conditions, the products formed from oxidative cleavage yield ___ chiral centers.
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Match the oxidative conditions with their appropriate method:
Match the oxidative conditions with their appropriate method:
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Which reagent is used in syn hydroxylation of alkenes?
Which reagent is used in syn hydroxylation of alkenes?
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Both syn and anti addition products from alkene reactions are chiral.
Both syn and anti addition products from alkene reactions are chiral.
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What is the typical number of chiral centers when using OsO4 for syn addition?
What is the typical number of chiral centers when using OsO4 for syn addition?
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In anti-addition reactions, the usual number of products formed is ___.
In anti-addition reactions, the usual number of products formed is ___.
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What is the result of oxidative cleavage under reducing conditions?
What is the result of oxidative cleavage under reducing conditions?
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Match the electrophilic addition reagents to their added components:
Match the electrophilic addition reagents to their added components:
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Match the reagents with their regioselectivity:
Match the reagents with their regioselectivity:
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Match the reagents with their intermediate types:
Match the reagents with their intermediate types:
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Match the reagent with its type of stereochemistry:
Match the reagent with its type of stereochemistry:
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Match the reagents with potential rearrangements:
Match the reagents with potential rearrangements:
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Match the reagent to its product nature:
Match the reagent to its product nature:
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Match the reagents with their used solvents or catalysts:
Match the reagents with their used solvents or catalysts:
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Match the reagents with their final product specificity:
Match the reagents with their final product specificity:
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Match the reaction conditions with the type of addition they produce:
Match the reaction conditions with the type of addition they produce:
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Match the reagents with their respective outcomes in oxidative cleavage of alkenes:
Match the reagents with their respective outcomes in oxidative cleavage of alkenes:
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Match the type of mechanism with its characteristic addition:
Match the type of mechanism with its characteristic addition:
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Match the products with the usual number of chiral centers formed:
Match the products with the usual number of chiral centers formed:
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Match the reagents with their specific types of addition:
Match the reagents with their specific types of addition:
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Match the oxidative cleavage conditions with their type:
Match the oxidative cleavage conditions with their type:
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Match the addition mechanism with their reagent:
Match the addition mechanism with their reagent:
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Study Notes
Alkenes Nomenclature
- Alkenes are identified by the suffix "-ene."
- Configuration designated as E/Z specifies the relative positioning of substituents around the double bond.
Electrophilic Addition Reactions
- Various reagents can add to alkenes via electrophilic addition, with each reaction having different characteristics.
Reagent Types and Characteristics
-
HBr, HCl, HI
- Adds H+ and Br-.
- Follows Markovnikov's rule for regioselectivity.
- Possible carbocation rearrangement.
-
H3O+
- Produces H+ and OH-.
- Also follows Markovnikov's rule with rearrangement possible.
-
H2 and ROH
- Adds H+ and OR- conforming to Markovnikov's rule with possible rearrangement.
-
Br2/CCl4 or Cl2
- Adds Br+ and Br- or Cl+ and Cl-.
- Anti addition (trans) through formation of a bromonium or chloronium ion.
- No rearrangement possible.
-
Br2/H2O and Cl2/H2O
- Adds Br+ and OH- or Cl+ and OH-.
- Markovnikov's rule applies, with anti addition.
-
Br2/ROH and Cl2/ROH
- Produces Br+ and OR- or Cl+ and OR-.
- Follows Markovnikov's rule with anti addition.
-
(1) Hg(OAc)2, H2O / (2) NaBH4
- Introduces H+ and OH-.
- Adheres to Markovnikov's rule with anti addition.
-
(1) BH3.THF / (2) H2O2, OH-, H2O
- Forms H+ and OH-.
- Anti-Markovnikov addition resulting in syn stereochemistry.
-
H2/catalyst (Pd/C, Pt/C, Ni)
- Hydrogenation resulting in syn addition of H and H.
-
HBr/ROOR (peroxide)
- Produces anti-Markovnikov addition of H and Br.
- Involves a radical mechanism.
-
RCO3H (MCPBA)
- Creates O via syn addition.
-
(1) RCO3H (MCPBA) / (2) H3O+
- Yields OH and OH through anti addition.
-
(1) OsO4 / (2) H2O2
- Generates OH and OH through syn addition.
-
KMnO4 (cold, dilute)/OH-
- Adds OH and OH in syn fashion.
Chiral Centers and Products
- No chiral centers lead to 1 product.
- One chiral center generates 2 products.
- Two chiral centers can create 2 syn products or 2 anti products, leading to a total of 4 products in syn or anti scenarios.
Oxidative Cleavage of Alkenes
-
Reducing Conditions:
- O3 followed by (CH3)2S or Zn/H2O cleaves alkenes.
-
Oxidizing Conditions:
- O3 followed by H2O2 or KMnO4 (hot, concentrated)/OH- or with H3O+ achieves oxidative cleavage.
Alkenes Nomenclature
- Alkenes are identified by the suffix "-ene."
- Configuration designated as E/Z specifies the relative positioning of substituents around the double bond.
Electrophilic Addition Reactions
- Various reagents can add to alkenes via electrophilic addition, with each reaction having different characteristics.
Reagent Types and Characteristics
-
HBr, HCl, HI
- Adds H+ and Br-.
- Follows Markovnikov's rule for regioselectivity.
- Possible carbocation rearrangement.
-
H3O+
- Produces H+ and OH-.
- Also follows Markovnikov's rule with rearrangement possible.
-
H2 and ROH
- Adds H+ and OR- conforming to Markovnikov's rule with possible rearrangement.
-
Br2/CCl4 or Cl2
- Adds Br+ and Br- or Cl+ and Cl-.
- Anti addition (trans) through formation of a bromonium or chloronium ion.
- No rearrangement possible.
-
Br2/H2O and Cl2/H2O
- Adds Br+ and OH- or Cl+ and OH-.
- Markovnikov's rule applies, with anti addition.
-
Br2/ROH and Cl2/ROH
- Produces Br+ and OR- or Cl+ and OR-.
- Follows Markovnikov's rule with anti addition.
-
(1) Hg(OAc)2, H2O / (2) NaBH4
- Introduces H+ and OH-.
- Adheres to Markovnikov's rule with anti addition.
-
(1) BH3.THF / (2) H2O2, OH-, H2O
- Forms H+ and OH-.
- Anti-Markovnikov addition resulting in syn stereochemistry.
-
H2/catalyst (Pd/C, Pt/C, Ni)
- Hydrogenation resulting in syn addition of H and H.
-
HBr/ROOR (peroxide)
- Produces anti-Markovnikov addition of H and Br.
- Involves a radical mechanism.
-
RCO3H (MCPBA)
- Creates O via syn addition.
-
(1) RCO3H (MCPBA) / (2) H3O+
- Yields OH and OH through anti addition.
-
(1) OsO4 / (2) H2O2
- Generates OH and OH through syn addition.
-
KMnO4 (cold, dilute)/OH-
- Adds OH and OH in syn fashion.
Chiral Centers and Products
- No chiral centers lead to 1 product.
- One chiral center generates 2 products.
- Two chiral centers can create 2 syn products or 2 anti products, leading to a total of 4 products in syn or anti scenarios.
Oxidative Cleavage of Alkenes
-
Reducing Conditions:
- O3 followed by (CH3)2S or Zn/H2O cleaves alkenes.
-
Oxidizing Conditions:
- O3 followed by H2O2 or KMnO4 (hot, concentrated)/OH- or with H3O+ achieves oxidative cleavage.
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Description
Test your knowledge on alkenes and alkynes, focusing on nomenclature and electrophilic addition reactions. Learn about the different reagents, regioselectivity, and intermediates involved in these important organic reactions.