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Questions and Answers
What suffix is commonly used in the nomenclature of alkenes?
Electrophilic addition of H2O to alkenes is always anti-addition.
False
What is the regioselectivity when adding HBr to an alkene?
Markovnikov
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:
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Which reaction leads to syn addition?
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Electrophilic addition reactions can involve carbocation rearrangement.
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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.
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Match the reagent with its type of selectivity:
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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.
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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.
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Match the oxidative conditions with their appropriate method:
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Which reagent is used in syn hydroxylation of alkenes?
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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?
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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?
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Match the electrophilic addition reagents to their added components:
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Match the reagents with their regioselectivity:
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Match the reagents with their intermediate types:
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Match the reagent with its type of stereochemistry:
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Match the reagents with potential rearrangements:
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Match the reagent to its product nature:
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Match the reagents with their used solvents or catalysts:
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Match the reagents with their final product specificity:
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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:
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Match the type of mechanism with its characteristic addition:
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Match the products with the usual number of chiral centers formed:
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Match the reagents with their specific types of addition:
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Match the oxidative cleavage conditions with their type:
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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.