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Questions and Answers
What reagent is used to convert an alkyl halide (methyl/1° unhindered) to alcohol?
What reagent is used to convert an alkyl halide (methyl/1° unhindered) to alcohol?
What reagents can convert an alkyl halide (1° hindered/2°) to alcohol?
What reagents can convert an alkyl halide (1° hindered/2°) to alcohol?
What reagent is needed to convert a 3° alkyl halide to alcohol?
What reagent is needed to convert a 3° alkyl halide to alcohol?
Which reagents can convert an alcohol to an alkene in its most stable Zaitsev configuration?
Which reagents can convert an alcohol to an alkene in its most stable Zaitsev configuration?
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What reagent can convert an alcohol to an alkyl halide?
What reagent can convert an alcohol to an alkyl halide?
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Which reagents are used to convert alcohol to an alkyl halide with inversion at the alpha carbon?
Which reagents are used to convert alcohol to an alkyl halide with inversion at the alpha carbon?
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What is needed to convert an alcohol to an alkyl halide while maintaining the alpha carbon configuration?
What is needed to convert an alcohol to an alkyl halide while maintaining the alpha carbon configuration?
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What type of nucleophile is necessary for converting an unhindered alkyl halide to Williamson ether?
What type of nucleophile is necessary for converting an unhindered alkyl halide to Williamson ether?
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What reagents are used to convert a symmetric ether to an alkyl halide?
What reagents are used to convert a symmetric ether to an alkyl halide?
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What reagents can convert an epoxide to an alcohol with inversion of the configuration?
What reagents can convert an epoxide to an alcohol with inversion of the configuration?
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Which acid is used to convert an epoxide to an alcohol attacking the more substituted side?
Which acid is used to convert an epoxide to an alcohol attacking the more substituted side?
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What reagents can convert an ester to a 1° alcohol?
What reagents can convert an ester to a 1° alcohol?
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What reagents can reduce an ester to a 3° alcohol?
What reagents can reduce an ester to a 3° alcohol?
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What reducing agent is used to convert a carboxylic acid to a 1° alcohol?
What reducing agent is used to convert a carboxylic acid to a 1° alcohol?
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Which reducing agent can convert an aldehyde to a 1° alcohol?
Which reducing agent can convert an aldehyde to a 1° alcohol?
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What reagent is used to convert an aldehyde to a 2° alcohol?
What reagent is used to convert an aldehyde to a 2° alcohol?
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Which reagent can reduce a ketone to a 2° alcohol?
Which reagent can reduce a ketone to a 2° alcohol?
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What reagent is used to convert a ketone to a 3° alcohol?
What reagent is used to convert a ketone to a 3° alcohol?
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What oxidizing agent can convert a 1° alcohol to a carboxylic acid?
What oxidizing agent can convert a 1° alcohol to a carboxylic acid?
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Which reagent is used to convert a 1° alcohol to an aldehyde?
Which reagent is used to convert a 1° alcohol to an aldehyde?
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What reagents are used to convert a 2° alcohol to a ketone?
What reagents are used to convert a 2° alcohol to a ketone?
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Which reagents can convert an aldehyde to a carboxylic acid?
Which reagents can convert an aldehyde to a carboxylic acid?
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What reagent is used to convert a carboxylic acid to a carboxylate?
What reagent is used to convert a carboxylic acid to a carboxylate?
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What are the components of PCC?
What are the components of PCC?
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What reactions does Jones reagent consist of?
What reactions does Jones reagent consist of?
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What reagents are used in Tollen's test?
What reagents are used in Tollen's test?
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What compounds are classified as organometallic reagents?
What compounds are classified as organometallic reagents?
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What reaction involves transforming b-hydroxy carbonyl to a-b-unsaturated carbonyl?
What reaction involves transforming b-hydroxy carbonyl to a-b-unsaturated carbonyl?
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What conditions are required to convert two aldehydes/ketones into b-hydroxy carbonyl?
What conditions are required to convert two aldehydes/ketones into b-hydroxy carbonyl?
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What reaction transforms two aldehydes/ketones into a,b-unsaturated carbonyl?
What reaction transforms two aldehydes/ketones into a,b-unsaturated carbonyl?
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What conditions yield multiple messy products from two aldehydes/ketones?
What conditions yield multiple messy products from two aldehydes/ketones?
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What condition leads to one product from two aldehydes/ketones?
What condition leads to one product from two aldehydes/ketones?
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What reagents facilitate the conversion of enone (a,b-unsaturated carbonyl) to less stable carbonyl?
What reagents facilitate the conversion of enone (a,b-unsaturated carbonyl) to less stable carbonyl?
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What reaction occurs to convert enone (a,b-unsaturated carbonyl) to a more stable carbonyl?
What reaction occurs to convert enone (a,b-unsaturated carbonyl) to a more stable carbonyl?
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Study Notes
Alkyl Halides and Alcohol Reactions
- Alkyl halide (methyl/1° unhindered) reacts with NaOH to form alcohol via Sn2 mechanism.
- Alkyl halide (1° hindered/2°) undergoes reaction with NaOAc and NaOH, resulting in alcohol through Sn2 then SnAc processes.
- Alkyl halide (3°) treated with H2O yields alcohol via Sn1 or E1 pathways.
Alcohol to Alkene Conversion
- Alcohol to alkene reaction achieves the most stable Zaitsev product using H2SO4 and heat.
- Alcohol transforms into alkyl halide using HCl (H-X); primary alcohols follow Sn2, while secondary and tertiary follow Sn1.
Alcohol Halogenation Reactions
- Alcohol reacts with PBr3 or PCl3 to yield alkyl halide, involving Sn2 mechanism with inversion at alpha carbon.
- Using SOCl2 and pyridine produces alkyl halide along with protonated pyridine and Cl ion, involving SnAc and Sn2 (inversion).
- ClMs, ClTs, or TfOTf applications yield alkyl halide with no change at the alpha carbon through SnAc and acid/base reactions.
Ether Reactions
- Unhindered alkyl halide produces Williamson ether using a strong alkoxide nucleophile.
- Symmetric ether reacts with H2SO4 and H2O to yield alkyl halide via Sn1 mechanism.
Epoxide Reactions
- Epoxide converts to alcohol through Sn2, with nucleophile attacking the less substituted side using strong bases like RS-, RO-, or OH-.
- Using strong acid (HCl) facilitates conversion of epoxide to alcohol with nucleophile attacking the more substituted side.
Ester and Carboxylic Acid Reductions
- Ester reduction forms 1° alcohol with two equivalents of LiAlH4.
- To yield 3° alcohol from ester, two organometallic reagents are used.
- Carboxylic acid reduction to 1° alcohol also requires two equivalents of LiAlH4.
- Aldehyde reduces to 1° alcohol utilizing either LiAlH4 or NaBH4; conversion to 2° alcohol requires organometallic reagents.
- Ketone reduces to 2° alcohol with LiAlH4 or NaBH4, while producing a 3° alcohol involves organometallic reagents.
Alcohol Oxidation
- 1° alcohol oxidation results in carboxylic acid through the Jones oxidation process.
- PCC is utilized to oxidize 1° alcohol to aldehyde.
- Jones or PCC can oxidize 2° alcohol into a ketone.
- Aldehyde oxidizes to carboxylic acid using Jones or Tollen's reagent (more selective).
Organometallic Chemistry
- Organometallic compounds such as R-MgBr, R-Li, and R-C≡C-Na are key reagents in various reduction reactions.
- Carboxylic acid to carboxylate conversion requires organometallic reagents.
Reaction Mechanisms and Products
- b-Hydroxy carbonyl converts to a,b-unsaturated carbonyl catalyzed by NaOH, heat, and water.
- Two aldehydes/ketones yield b-hydroxy carbonyl under NaOH and water catalysis.
- Two aldehydes/ketones can produce a,b-unsaturated carbonyl with acidic conditions (H3O+, H2O).
- Conditions may lead to multiple messy products with two aldehydes/ketones treated with NaOH, heat, and water.
- If alpha H's on carbon attached to C=O are present, use nucleophiles; otherwise, participate as an electrophile under NaOH, heat, and water.
Addition Reactions of Enones
- Enone to carbonyl type conversion can occur via 1,2 addition yielding less stable alkene using LiAlH4, R-MgBr, or R-Li.
- For more stable alkene formation (1,4 addition), utilize good nucleophiles and weak bases such as RS-, -CN, R2NH, or HBr.
Studying That Suits You
Use AI to generate personalized quizzes and flashcards to suit your learning preferences.
Description
Test your knowledge of organic reactions with these reagent flashcards. Each card provides a specific reagent and the corresponding reaction pathway. Ideal for students studying organic chemistry and reaction mechanisms.
