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Questions and Answers
What is the main use of DIBAL-H (diisobutylaluminum hydride) in organic chemistry?
Which reagent is typically used for the bromination of alkenes?
What is the primary role of Cu2X2 (copper(II) halide) in organic synthesis?
Which reagent is typically used for the Friedel-Crafts acylation of aromatic compounds?
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What is the primary use of chromium trioxide (CrO3) in organic chemistry?
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Which reagent is typically used for the Simmons-Smith cyclopropanation reaction?
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What is the primary use of diazomethane (CH2N2) in organic synthesis?
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Which reagent is typically used for the Jones oxidation of alcohols?
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What is the primary use of borane (BH3) in organic chemistry?
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Which reagent is typically used for the Wolff-Kishner reduction of aldehydes and ketones?
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Study Notes
Friedel-Crafts Reaction and Electrophilic Aromatic Substitution
- AlCl3 and AlBr3 are strong Lewis acids utilized as catalysts.
- Carbocation intermediates form during these reactions; rearrangement is possible.
Hydroboration Reaction
- BH3 and CH2 are used for hydroboration in the presence of H2O2/KOH.
- Tetrahydrofuran (THF) is used to facilitate the reaction by breaking dimer B2H6.
- Dialkylboranes (R2BH), such as 9-BBN or isoamylborane, prevent excessive addition to alkynes.
Bromination Reactions
- Anti-addition occurs with alkenes and alkynes in solvents like CCl4 and CH2Cl2.
- Vicinal dibromide formation involves Br2 and water, leading to regioselective reactions.
Haloform Reaction
- Bromine (Br2) converts methyl ketones to haloforms (CHX3) and carboxylic acid salts.
Hoffmann Bromamide Degradation
- Converts primary amides into primary amines with a loss of one carbon atom.
Hell–Volhard–Zelinski (HVZ) Reaction
- Produces tetrabromides from compounds in the presence of Br2.
Preparation of Cyanides
- Cyanide ions and nitriles are produced by reacting compounds with acidic solutions, using various chromium compounds (e.g., CrO3/H3O+).
Cupurous Halides (Cu2X2)
- Employed in reactions of arene diazonium salts.
Dimethyl Sulfide (DMS)
- Serves a role in reductive ozonolysis, yielding carbonyl compounds from alkenes.
Diazomethane (CH2N2)
- Used for methyl-esterification of carboxylic acids and cyclopropanation of alkenes.
Hydrogenation
- Dihydrogen (H2) reduces alkenes and alkynes to alkanes using metal catalysts like Pd, Pt, or Ni.
- The process facilitates the insertion of methylene into the OH bond of phenols.
DIBAL-H (Di-isobutyl aluminum hydride)
- Reduces esters to aldehydes and is crucial for controlling selectivity in reductions.
Reduction of Nitriles
- Nitriles convert to primary amines via catalytic hydrogenation, providing a pathway for ascending aminated series.
Reduction Conditions
- Trans alkenes are formed from triple bonds through reduction with sodium in liquid ammonia.
Iron (Fe)
- An important reagent in various organic reactions but specific information is not provided in the text.
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Description
Test your understanding of the role of AlCl3 in Friedel-Crafts Reaction and Electrophilic Aromatic Substitution (EAS) Alkylation. Learn about the formation of carbocation intermediates and the use of catalysts in these reactions.
