Questions and Answers
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 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?
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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?
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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?
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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?
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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?
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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?
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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?
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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?
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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?
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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?
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What reagent is used to convert a carboxylic acid to a carboxylate?
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What are the components of PCC?
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What reactions does Jones reagent consist of?
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What reagents are used in Tollen's test?
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What compounds are classified as organometallic reagents?
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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?
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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?
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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?
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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.
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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.
