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All Orgo Equations
| Question | Answer |
|---|---|
| HX (HCl, HBr, HI) | Hydrohalogenation. Markovnikov addition — H adds to less substituted carbon, X adds to more substituted carbon. Carbocation rearrangement possible. |
| HBr + ROOR (peroxide) | Radical addition. Anti-Markovnikov — H adds to more substituted carbon, Br adds to less substituted carbon. Only works with HBr. |
| H₂O + catalytic acid (H₂SO₄ or H₃O⁺) | Acid catalyzed hydration. Markovnikov addition of H and OH → alcohol. Carbocation rearrangement possible. No stereoselectivity. |
| ROH + catalytic acid | Acid catalyzed addition of alcohol. Markovnikov addition of H and OR. Carbocation rearrangement possible. |
| 1) Hg(OAc)₂, H₂O, THF → 2) NaBH₄ | Oxymercuration-demercuration. Markovnikov addition of H and OH. No rearrangements. Stereorandom. |
| 1) BH₃, THF → 2) H₂O₂, NaOH | Hydroboration-oxidation. Anti-Markovnikov addition of H and OH. No rearrangements. Syn addition only. |
| Br₂ or Cl₂ in CCl₄ | Dihalogenation. Adds X and X → vicinal dihalide. Anti addition only. Halonium ion intermediate. |
| Br₂ or Cl₂ + H₂O | Halohydrin formation. Adds X and OH. Anti addition. OH always goes to the more substituted carbon. |
| RCO₃H (e.g. mCPBA) | Epoxidation. Forms an epoxide. Both enantiomers produced if product is chiral. |
| 1) mCPBA → 2) H₃O⁺ or NaOH/H₂O | Anti dihydroxylation. Adds two OH groups → vicinal diol. Anti addition. |
| Cold KMnO₄ / NaOH | Syn dihydroxylation. Adds two OH groups → vicinal diol. Syn addition. |
| 1) OsO₄ → 2) H₂O₂ or NaHSO₃/H₂O | Anti dihydroxylation. Adds two OH groups → vicinal diol. Anti addition. |
| 1) O₃ → 2) DMS or Zn/HOAc | Ozonolysis, reductive workup. Cleaves double bond. Carbon bonded to H → aldehyde. Carbon bonded to two carbons → ketone. |
| 1) O₃ → 2) H₂O₂ | Ozonolysis, oxidative workup. Cleaves double bond. Carbon bonded to H → carboxylic acid. Carbon bonded to two carbons → ketone. |
| Hot KMnO₄ | acidic workup. Oxidative cleavage. Same result as ozonolysis with oxidative workup — carboxylic acid or ketone depending on substitution. |
| H₂ + Pd, Pd/C, or Pt | Catalytic hydrogenation. Reduces alkene → alkane. Syn addition. Both enantiomers formed. |
| Terminal alkyne + HX (1 equiv.), no peroxide | Markovnikov vinyl halide (X on more substituted carbon) — alkene |
| Terminal alkyne + HX (2 equiv.), no peroxide | Geminal dihalide (both X on same carbon, more substituted) — alkane |
| Terminal alkyne + HBr / ROOR (1 equiv.) | Anti-Markovnikov vinyl halide (Br on terminal carbon) — alkene |
| Terminal alkyne + HBr / ROOR (2 equiv.) | Geminal dihalide (both Br on terminal carbon) — alkane |
| Unsymmetrical internal alkyne + HX (1 equiv.) | Mixture of two vinyl halide products — alkenes |
| Symmetrical internal alkyne + HX (1 equiv.) | One vinyl halide product only — alkene |
| Alkyne + excess Cl₂ or Br₂ (≥2 equiv.) | Tetrahaloalkane (four total halogens, two on each alkyne carbon) — alkane |
| Alkyne + H₂ / Pd, Pd/C, or Pt | Full reduction — alkane |
| Alkyne + H₂ / Lindlar's catalyst | cis/Z — alkene |
| Alkyne + Li or Na / liquid NH₃ | trans/E — alkene |
| Terminal alkyne + HgSO₄ / H₂SO₄, H₂O | Enol → tautomerizes to ketone (Markovnikov) — ketone (carbonyl) |
| Terminal alkyne + R₂BH (Sia₂BH or 9-BBN) / THF, then H₂O₂ / NaOH | Enol → tautomerizes to aldehyde (anti-Markovnikov) — aldehyde (carbonyl) |
| Terminal alkyne + 1) O₃ → 2) H₂O | Carboxylic acid + CO₂ — carboxylic acid |
| Unsymmetrical internal alkyne + 1) O₃ → 2) H₂O | Two different carboxylic acids — carboxylic acids |
| Symmetrical internal alkyne + 1) O₃ → 2) H₂O | Two equivalents of the same carboxylic acid — carboxylic acid |
| Terminal alkyne + NaNH₂ or NaH | Acetylide ion (deprotonated terminal carbon) — alkyne anion |
| Acetylide ion + methyl or primary alkyl halide | Elongated carbon chain via SN2 — alkyne |
| What is the product when a primary alcohol is treated with PCC, DMP/CH₂Cl₂, or Swern oxidation (DMSO/(COCl)₂, then NEt₃)? | An aldehyde |
| What is the product when a primary alcohol is treated with a strong oxidizing agent (KMnO₄, K₂Cr₂O₇, Na₂Cr₂O₇, H₂CrO₄, or CrO₃/H₂SO₄)? | A carboxylic acid |
| What is the product when a secondary alcohol is treated with any oxidizing agent? | A ketone |
| What happens when a tertiary alcohol is treated with an oxidizing agent? | No reaction — tertiary alcohols cannot be oxidized |
| What is the product when a ketone or aldehyde is treated with NaBH₄ or LiAlH₄, followed by H₃O⁺ workup? | Ketone → secondary alcohol; Aldehyde → primary alcohol |
| What is the product when an ester or carboxylic acid is treated with LiAlH₄, then H₃O⁺? | A primary alcohol |
| What is the product when an ester or carboxylic acid is treated with NaBH₄, then H₃O⁺? | No reaction — NaBH₄ is too weak to reduce esters or carboxylic acids |
| What are the reagents and product of a Clemmensen reduction? Reagents: Zn(Hg) and HCl. | The carbonyl group (ketone or aldehyde) is reduced to an alkane |
| What are the reagents and product of a Wolff-Kishner reduction? Reagents: H₂NNH₂ (hydrazine) and KOH/heat. | Product: The carbonyl group (ketone or aldehyde) is reduced to an alkane |
| What is the product when an aldehyde or ketone is reacted with an alcohol under basic conditions? | A hemi-acetal (from aldehyde) or hemi-ketal (from ketone) |
| What is the product when an aldehyde or ketone is reacted with an alcohol under acidic conditions (cat. H⁺)? | An acetal (from aldehyde) or ketal (from ketone) — the carbonyl oxygen is replaced by two alkoxy groups |
| What is the product when an acetal or ketal is treated with H₃O⁺ (aqueous acid)? | The original aldehyde or ketone is regenerated (hydrolysis) |
| What is the product when a ketone or aldehyde reacts with a diol under acidic conditions (e.g., H₂SO₄)? | A cyclic acetal or cyclic ketal (used as a protecting group) |
| What is the product when an aldehyde or ketone is reacted with a primary amine (1° amine) with catalytic acid? | An imine (contains a C=N double bond) |
| What is the product when an aldehyde or ketone is reacted with a secondary amine (2° amine) with catalytic acid? | An enamine (contains a C=C double bond with nitrogen single-bonded to one alkene carbon) |
| What is the product when an imine or enamine is treated with H₂O and catalytic acid? | The original ketone (hydrolysis) |
| How is a Grignard reagent formed, and what are the conditions? | An alkyl halide is reacted with elemental magnesium (Mg) in an aprotic solvent (THF or Et₂O), producing R-MgBr |
| What is the product when a Grignard reagent attacks an aldehyde or ketone, followed by H₃O⁺ workup? | An alcohol (the alkyl group from the Grignard adds to the carbonyl carbon) |
| What happens when a Grignard reagent is exposed to water or other acidic protons? | The Grignard is destroyed — it abstracts a proton from water and produces an alkane, ruining the reagent |
| What is the product of the Wittig reaction between a Wittig reagent (ylide) and an aldehyde or ketone? | There's a double bond where the O was and the section originally attached to the PPh₃, P=O is released as a byproduct |
| What is a hemi-acetal? | An aldehyde that reacted with one alcohol. Has both -OH and -OR on the same carbon. |
| What is an acetal? | An aldehyde that reacted with two alcohols. Has two -OR groups on the same carbon, no -OH. |
| What is a hemi-ketal? | A ketone that reacted with one alcohol. Has both -OH and -OR on the same carbon. |
| What is a ketal? | A ketone that reacted with two alcohols. Has two -OR groups on the same carbon, no -OH. |
| KMnO₄, H₂CrO₄, or CrO₃/H₂SO₄ (Jones reagent) acting on a primary alcohol | Carboxylic acid |
| 1) Mg, 2) CO₂, 3) H₃O⁺ acting on an alkyl halide | Carboxylic acid (via Grignard reagent) |
| SOCl₂ or PCl₃ acting on a carboxylic acid | Acid chloride |
| H₃O⁺ (or 1) NaOH, 2) H₃O⁺) acting on an acid chloride or acid anhydride | Carboxylic acid |
| ROH with [H⁺], or 1) NaOR, 2) H₃O⁺ acting on an acid chloride or acid anhydride | Ester |
| R₂NH acting on an acid chloride or acid anhydride | Amide |
| 1) excess LiAlH₄, 2) H₃O⁺ acting on an acid chloride or acid anhydride | Primary alcohol |
| 1) excess RMgX, 2) H₃O⁺ acting on an acid chloride or acid anhydride | Tertiary alcohol |
| R₂CuLi acting on an acid chloride or acid anhydride | Ketone |
| ROH with [H⁺] acting on a carboxylic acid | Ester + H₂O (Fischer esterification) |
| 1) NaOH, 2) H₃O⁺ acting on an ester | Carboxylic acid (saponification) |
| Acid or base with alcohol acting on an ester | New ester with replaced alkoxy group (transesterification) |
| 1) 2 eq. Grignard (RMgX), 2) H₃O⁺ acting on an acid chloride, acid anhydride, or ester | Tertiary alcohol (goes through ketone intermediate) |
| 1) LiAlH₄, 2) H₃O⁺ acting on an ester | Primary alcohol |
| 1) LiAlH₄, 2) H₃O⁺ acting on an acid chloride | Primary alcohol |
| 1) LiAlH₄, 2) H₂O acting on an amide | Amine |
| 1) DIBAL-H at −70°C, 2) H₂O acting on an ester | Aldehyde |
| 1) LTBA, 2) H₂O acting on an acid chloride | Aldehyde |
| Br₂ / NaOH acting on a primary amide | (Hofmann rearrangement) Primary amine (one carbon shorter; carbonyl carbon is lost) |
| Cyanide ion (NaCN) acting on an alkyl halide | Nitrile |
| 1) LiAlH₄, 2) H₂O acting on a nitrile | Primary amine |
| H₃O⁺ with heat acting on a nitrile | Carboxylic acid (nitrile hydrolysis) |
| HCN acting on an aldehyde or ketone | Cyanohydrin (−OH and −CN on the same carbon) |
| 1) Grignard reagent (RMgX), 2) H₃O⁺ acting on a nitrile | Ketone (via imine intermediate) |
| H₂O / acidic aqueous conditions with heat acting on an amide (amide hydrolysis) | Carboxylic acid |
| HI / HBr / HCl + alcohol | Converts alcohol to alkyl halide. Tertiary/secondary → SN1; primary → SN2. Requires protonation of OH first. |
| PBr3 + primary or secondary alcohol | Converts to alkyl bromide with inversion of stereochemistry (SN2). |
| SOCl2 + primary or secondary alcohol | Converts to alkyl chloride with inversion of stereochemistry (SN2). |
| TsCl (tosyl chloride) + alcohol | Converts OH to tosylate (good leaving group) with retention of stereochemistry. |
| MsCl (mesyl chloride) + alcohol | Converts OH to mesylate (good leaving group) with retention of stereochemistry. |
| NaH + alcohol, then alkyl halide (Williamson Ether Synthesis) | Deprotonates alcohol to form alkoxide, which attacks alkyl halide via SN2 to form an ether. |
| Strong acid (H⁺) + primary alcohol | Protonates OH; second alcohol molecule attacks via SN2, water leaves — forms a symmetrical ether. |
| HBr or HI (excess) + ether | Cleaves ether into two alkyl halides. HCl and HF cannot do this. |
| HBr or HI + aryl/vinyl ether | Cleaves to give one alkyl halide + one alcohol (aryl/vinyl carbon cannot undergo nucleophilic attack). |
| mCPBA + alkene | Epoxidizes the double bond, forming an epoxide. |
| Nucleophile + epoxide in basic conditions | SN2 attack at the less substituted carbon; followed by acidic workup to protonate the alkoxide. |
| Grignard reagent (RMgBr) + epoxide | Basic conditions; attacks less substituted carbon SN2 style, then H₃O⁺ workup gives alcohol. (Grignard cannot exist in acidic conditions.) |
| Organolithium (RLi) or LiAlH₄ + epoxide | Same as Grignard — basic conditions, attacks less substituted carbon, acidic workup. |
| Nucleophile + epoxide in acidic conditions (e.g., HCl, H₂O/H⁺, ROH/H⁺) | Epoxide oxygen is protonated first, weakening the bond to the more substituted carbon; nucleophile attacks the more substituted carbon via SN2. |
| NaOCH₃ (or NaOR) + epoxide | Basic conditions; methoxide attacks less substituted carbon, acidic workup gives a β-methoxy alcohol. |
| CH₃OH + H⁺ + epoxide | Acidic conditions; methanol attacks more substituted carbon, giving a β-methoxy alcohol (regiochemistry opposite to basic conditions). |
Created by:
smurtab