Organic Chemistry 2 · Functional-group transformations
Oxidation and reduction toolkit: practice problems
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- PCC oxidation of butan-1-ol to butanal
- Baeyer–Villiger oxidation of acetophenone to phenyl acetate
- LiAlH4 reduction of ethyl benzoate to benzyl alcohol
- Wolff–Kishner reduction of acetophenone to ethylbenzene
- Baeyer–Villiger oxidation of cyclohexanone to ε-caprolactone
- Chromic acid oxidation of propan-2-ol to acetone
- DIBAL-H partial reduction of methyl hexanoate to hexanal
- Jones oxidation of butan-1-ol to butanoic acid
- LiAlH4 reduction of 2-piperidone to piperidine
Draw the mechanism 72
- Baeyer–Villiger oxidation of cyclohexanone to ε-caprolactoneDraw the Baeyer–Villiger oxidation of cyclohexanone by mCPBA: protonation and addition to give the Criegee intermediate, then the concerted migration of a ring carbon to oxygen that expands the ring to ε-caprolactone.
- Chromic acid oxidation of propan-2-ol to acetoneDraw formation of the chromate ester of propan-2-ol from chromic acid in aqueous acid, then the E2-like removal of the carbinol hydrogen by water that gives acetone and reduced chromium.
- DIBAL-H partial reduction of methyl hexanoate to hexanalDraw coordination of DIBAL-H to methyl hexanoate, hydride transfer to the stable aluminium hemiacetal, and the acidic workup that releases hexanal.
- Jones oxidation of butan-1-ol to butanoic acidDraw the Jones oxidation of butan-1-ol through butanal and its hydrate: chromate ester formation, elimination, acid-catalysed hydration, a second chromate ester and a second elimination that give butanoic acid.
- LiAlH4 reduction of 2-piperidone to piperidineDraw the LiAlH4 reduction of the lactam 2-piperidone: N–H deprotonation by hydride, activation of oxygen by aluminium, hydride addition, loss of the oxygen as an aluminate to form an imine, the second hydride addition and protonation, giving piperidine.
- LiAlH4 reduction of butanenitrile to butan-1-amineDraw two hydride additions to the nitrile carbon of butanenitrile and the two proton transfers from water that give butan-1-amine.
- LiAlH4 reduction of γ-butyrolactone to butane-1,4-diolDraw the LiAlH4 reduction of γ-butyrolactone: hydride addition, ring opening of the tetrahedral intermediate to an alkoxy aldehyde, the second hydride addition and the water workup that gives butane-1,4-diol.
- LiAlH4 reduction of hexanoic acid to hexan-1-olDraw the LiAlH4 reduction of hexanoic acid: deprotonation of the acid with loss of H2, activation of the carboxylate by aluminium, hydride addition, collapse to hexanal, a second hydride addition and acidic workup to hexan-1-ol.
- LiAlH4 reduction of methyl acetate to ethanol and methanolDraw both hydride additions in the LiAlH4 reduction of methyl acetate, including loss of methoxide from the tetrahedral intermediate, and the water workup that gives ethanol and methanol.
- LiAlH4 opens 2-methyloxirane to propan-2-olDraw the SN2 opening of 2-methyloxirane by hydride at the less hindered carbon and the water workup that gives propan-2-ol.
- Meerwein–Ponndorf–Verley reduction of cyclohexanoneDraw the Meerwein–Ponndorf–Verley reduction of cyclohexanone: coordination to aluminium isopropoxide, the cyclic hydride transfer that releases acetone, and the exchange with isopropanol that frees cyclohexanol.
- NaBH4 reduces the aldehyde of methyl 4-formylbenzoateDraw hydride addition from borohydride to the aldehyde carbon of methyl 4-formylbenzoate and protonation of the alkoxide by methanol, giving methyl 4-(hydroxymethyl)benzoate.
- NaBH4 reduction of acetone to propan-2-olDraw hydride transfer from borohydride to the carbonyl carbon of acetone and protonation of the alkoxide by methanol, giving propan-2-ol.
- NaBH4 reduction of 4-oxopentanoic acid in aqueous baseDraw deprotonation of 4-oxopentanoic acid by hydroxide, hydride addition to the ketone, protonation of the alkoxide by water, and acidification of the carboxylate, giving 4-hydroxypentanoic acid.
- Chemoselective NaBH4 reduction of methyl 4-oxopentanoateDraw hydride delivery from borohydride to the ketone carbon of methyl 4-oxopentanoate and protonation of the alkoxide by methanol, leaving the methyl ester untouched.
- PCC oxidation of butan-1-ol to butanalDraw the PCC oxidation of butan-1-ol: chromate ester formation with loss of chloride, then the E2-like removal of the carbinol hydrogen by pyridine that gives butanal.
- Swern oxidation of cyclohexanol to cyclohexanoneDraw the Swern oxidation of cyclohexanol: activation of DMSO by oxalyl chloride to the chlorodimethylsulfonium ion, formation of the alkoxysulfonium ion, ylide formation with triethylamine and the intramolecular hydrogen transfer that gives cyclohexanone and dimethyl sulfide.
- Wolff–Kishner reduction of 1-tetralone to tetralinDraw the Wolff–Kishner reduction of 1-tetralone: hydrazone formation under basic conditions, then the deprotonation, carbon protonation and N2 loss that convert the C=O carbon into a CH2 group of tetralin.
- Baeyer–Villiger oxidation of acetophenone to phenyl acetateDraw protonation of acetophenone by mCPBA, addition of the peroxy anion to give the Criegee intermediate, migration of the phenyl group to oxygen with loss of 3-chlorobenzoate, and the final deprotonation to phenyl acetate.
- Barton–McCombie radical chain on cyclohexyl xanthateDraw the initiation and propagation steps of the tributyltin radical chain that deoxygenates O-cyclohexyl S-methyl xanthate to cyclohexane, using fishhook arrows for every one-electron move.
- Barton–McCombie deoxygenation of octan-2-ol to octaneDraw the conversion of octan-2-ol into its S-methyl xanthate with NaH, CS2 and MeI, then the AIBN-initiated tributyltin radical chain that cleaves the C–O bond and gives octane.
- Chemoselective borane reduction of monoethyl terephthalateDraw the chemoselective BH3·THF reduction of monoethyl terephthalate: acyloxyborane formation with loss of H2, hydroboration of that C=O, collapse to the aldehyde, its reduction and the water workup, with the ethyl ester untouched.
- Borane reduction of phenylacetic acid to 2-phenylethanolDraw the BH3·THF reduction of phenylacetic acid: acyloxyborane formation with loss of H2, hydroboration of the C=O, collapse to phenylacetaldehyde, its reduction by borane and the water workup that gives 2-phenylethanol.
- Catecholborane hydroboration of 4-phenylbut-1-yneDraw the thermal hydroboration of 4-phenylbut-1-yne by catecholborane, the H2O2/NaOH oxidation of the alkenyl boronate and the enol-to-aldehyde step that gives 4-phenylbutanal.
- Clemmensen reduction of 1-indanone to indaneFollow a schematic of the zinc-surface Clemmensen reduction of 1-indanone: carbonyl protonation, electron transfer from zinc, loss of water and protonation of the C–Zn bonds to give indane.
- Clemmensen reduction of 4-hydroxyacetophenoneFollow a schematic of the zinc-surface Clemmensen reduction that turns the acetyl C=O of 4-hydroxyacetophenone into CH2, giving 4-ethylphenol with the phenol OH untouched.
- Corey–Kim oxidation of cyclopentanol to cyclopentanoneDraw the Corey–Kim oxidation of cyclopentanol: chlorodimethylsulfonium ion from NCS and dimethyl sulfide, the alkoxysulfonium ion, the sulfur ylide made by triethylamine and the intramolecular hydrogen transfer that gives cyclopentanone.
- Corey–Kim oxidation of octan-1-ol to octanalDraw the Corey–Kim oxidation of octan-1-ol: chlorodimethylsulfonium ion from NCS and dimethyl sulfide, the alkoxysulfonium ion, the sulfur ylide and the intramolecular hydrogen transfer that stops at octanal.
- Dess–Martin oxidation of benzyl alcohol to benzaldehydeDraw ligand exchange of benzyl alcohol onto the iodine(V) of Dess–Martin periodinane, deprotonation, loss of a second acetate, and the acetate-mediated elimination that gives benzaldehyde and an iodine(III) by-product.
- DIBAL-H reduction of cyclohexanecarbonitrile to the aldehydeDraw the DIBAL-H reduction of cyclohexanecarbonitrile: coordination of the nitrile nitrogen to aluminium, one hydride transfer to the N-aluminium imine, and the acidic workup that hydrolyses the imine to cyclohexanecarbaldehyde.
- DIBAL-H reduction of γ-butyrolactone to the lactolDraw the DIBAL-H reduction of γ-butyrolactone at −78 °C: coordination of the carbonyl oxygen to aluminium, hydride transfer to the stable tetrahedral aluminium acetal and the water workup that releases the lactol oxolan-2-ol.
- Hydroboration–oxidation of 5-chloropent-1-yneDraw the single anti-Markovnikov hydroboration of 5-chloropent-1-yne by disiamylborane, the oxidation of the alkenylborane and the enol-to-aldehyde tautomerisation that gives 5-chloropentanal.
- Bleach oxidation of cyclododecanol to cyclododecanoneDraw the hypochlorite (bleach) oxidation of cyclododecanol in acetic acid: formation of HOCl, the alkyl hypochlorite, and the E2-like loss of chloride that gives cyclododecanone.
- IBX oxidation of cinnamyl alcohol to cinnamaldehydeDraw the IBX oxidation of (E)-cinnamyl alcohol: ligand exchange at iodine(V), proton transfer to hydroxide and the oxo-assisted removal of the carbinol hydrogen that gives (E)-cinnamaldehyde and IBA.
- IBX oxidation of octan-2-ol to octan-2-oneDraw the IBX oxidation of octan-2-ol in ethyl acetate: ligand exchange at iodine(V), proton transfer to hydroxide and the oxo-assisted removal of the carbinol hydrogen that gives octan-2-one and IBA.
- Et3SiH/TFA deoxygenation of 1-(4-methoxyphenyl)ethanolDraw how trifluoroacetic acid turns 1-(4-methoxyphenyl)ethanol into a resonance-stabilised benzylic cation and how triethylsilane delivers hydride to it, giving 4-ethylanisole.
- Jones oxidation of cyclohexanol to cyclohexanoneDraw formation of the chromate ester of cyclohexanol from chromic acid, the proton transfer to the chromium oxide, and the E2-like removal of the carbinol hydrogen by water that gives cyclohexanone.
- Cold KMnO4 dihydroxylation of cyclopentene to cis-cyclopentane-1,2-diolDraw the concerted [3+2] cycloaddition of permanganate to cyclopentene and the base hydrolysis of both Mn–O bonds of the cyclic manganate ester, giving cis-cyclopentane-1,2-diol.
- KMnO4 oxidation of propan-1-ol to propanoic acidDraw the manganate-ester oxidation of propan-1-ol to propanal, hydration of propanal, a second manganate-ester oxidation of the hydrate to propanoic acid, its deprotonation in base, and protonation in the acidic workup.
- Lemieux–Johnson cleavage of oct-1-ene to heptanalDraw the OsO4 dihydroxylation of oct-1-ene, then the cyclic periodate ester of octane-1,2-diol and its fragmentation into heptanal and formaldehyde, an ozone-free alternative to ozonolysis.
- LiAlH(Ot-Bu)3 reduction of benzoyl chloride to benzaldehydeDraw the reduction of benzoyl chloride with lithium tri-tert-butoxyaluminium hydride at −78 °C: one hydride addition to the acyl chloride carbon and loss of chloride from the tetrahedral alkoxide, giving benzaldehyde.
- LiAlH4 reduces 1-bromobutane to butaneDraw the one-step backside displacement of bromide from 1-bromobutane by a hydride from aluminohydride, giving butane.
- LiAlH4 deoxygenates cyclohexyl tosylate to cyclohexaneDraw the backside displacement of the tosylate group of cyclohexyl tosylate by hydride from aluminohydride, giving cyclohexane and the tosylate anion.
- LiAlH4 reduction of N,N-dimethylbenzamide to N,N-dimethylbenzylamineDraw hydride addition to the amide carbon, coordination of the alkoxide to aluminium, loss of the oxygen as an aluminate to form an iminium ion, and a second hydride addition giving N,N-dimethylbenzylamine.
- LiAlH4 reduction of ethyl benzoate to benzyl alcoholDraw two hydride additions to ethyl benzoate with loss of ethoxide in between, then protonation of both alkoxides in the aqueous workup to give benzyl alcohol and ethanol.
- LiAlH4 reduction of methyl phenylacetate to 2-phenylethanolDraw the LiAlH4 reduction of methyl phenylacetate: hydride addition, loss of methoxide to phenylacetaldehyde, a second hydride addition and the water workup that gives 2-phenylethanol and methanol.
- Lindlar hydrogenation of hex-3-yne to (Z)-hex-3-eneShow, as a schematic of the surface reaction, the H–H bond splitting and both hydrogen atoms adding to the same face of hex-3-yne so that (Z)-hex-3-ene forms and is not reduced further.
- Luche reduction of (E)-chalcone to the allylic alcoholDraw the Luche reduction of (E)-chalcone: 1,2-hydride addition of borohydride to the Ce3+-activated carbonyl carbon and protonation of the alkoxide by methanol, giving (E)-1,3-diphenylprop-2-en-1-ol.
- Mozingo reduction of 2-methylcyclohexanoneDraw how BF3 and ethane-1,2-dithiol convert 2-methylcyclohexanone into its spiro dithiolane, and the schematic Raney nickel C–S hydrogenolysis that leaves methylcyclohexane.
- Mozingo reduction of 4-tert-butylcyclohexanoneDraw the BF3-promoted formation of the 1,3-dithiolane from 4-tert-butylcyclohexanone and ethane-1,2-dithiol, then the schematic Raney nickel hydrogenolysis of its C–S bonds to tert-butylcyclohexane.
- NaBH4 reduction of 4-chlorobenzaldehydeDraw the NaBH4 reduction of 4-chlorobenzaldehyde in ethanol: hydride addition to the aldehyde carbon and protonation of the alkoxide by ethanol, giving (4-chlorophenyl)methanol with the C–Cl bond intact.
- NaBH4 reduction of acetophenone to 1-phenylethanolDraw hydride transfer from borohydride to the ketone carbon of acetophenone, then protonation of the alkoxide by ethanol to give racemic 1-phenylethanol.
- NaBH4 reduction of hexanal to hexan-1-olDraw the NaBH4 reduction of hexanal in methanol: hydride addition from borohydride to the aldehyde carbon and protonation of the alkoxide by methanol, giving hexan-1-ol.
- NaBH4 reduces the ketone of 4-nitroacetophenoneDraw hydride transfer from borohydride to the ketone carbon of 4-nitroacetophenone and protonation of the alkoxide by methanol, leaving the nitro group untouched.
- Oppenauer oxidation of cyclohexanol to cyclohexanoneDraw exchange of cyclohexanol onto aluminium isopropoxide, coordination of acetone to aluminium, and the six-membered hydride transfer that gives cyclohexanone and an aluminium isopropoxide.
- OsO4 dihydroxylation of cyclohexene to cis-cyclohexane-1,2-diolDraw the concerted [3+2] cycloaddition of OsO4 to cyclohexene and the hydrolysis of both Os–O bonds of the cyclic osmate ester, giving cis-cyclohexane-1,2-diol.
- Ozonolysis of cyclohexene to hexanedialDraw the cycloaddition of ozone to cyclohexene, the fragmentation of the molozonide to a carbonyl oxide and an aldehyde, their recombination to the ozonide, and the reduction of the ozonide by dimethyl sulfide to hexanedial.
- Parikh–Doering oxidation of 2-phenylethanolDraw the Parikh–Doering oxidation of 2-phenylethanol: activation of DMSO by SO3, the alkoxysulfonium ion, the sulfur ylide made by triethylamine and the intramolecular elimination that gives phenylacetaldehyde.
- Parikh–Doering oxidation of 4-tert-butylcyclohexanolDraw the Parikh–Doering oxidation of 4-tert-butylcyclohexanol: DMSO activated by SO3, the alkoxysulfonium ion, the ylide made by Hünig’s base and the elimination that gives 4-tert-butylcyclohexanone.
- PCC oxidation of cyclohexylmethanol to the aldehydeDraw the PCC oxidation of cyclohexylmethanol: chromate ester formation, proton transfer to the chromium oxide and the E2-like removal of the carbinol hydrogen that gives cyclohexanecarbaldehyde.
- Pinnick oxidation of benzaldehyde to benzoic acidDraw protonation of benzaldehyde by chlorous acid, addition of chlorite to the carbonyl carbon, and the pericyclic fragmentation that gives benzoic acid and hypochlorous acid.
- Pinnick oxidation of (E)-hex-2-enal to (E)-hex-2-enoic acidDraw the Pinnick oxidation of (E)-hex-2-enal: protonation by chlorous acid, addition of chlorite to the aldehyde carbon and the pericyclic fragmentation that gives (E)-hex-2-enoic acid and HOCl.
- Red-Al trans reduction of but-2-yn-1-olDraw how Red-Al first deprotonates but-2-yn-1-ol, then delivers hydride intramolecularly to the alkyne to form a trans oxaaluminacycle, and how water releases (E)-but-2-en-1-ol.
- Red-Al reduction of methyl 4-methylbenzoateDraw the Red-Al reduction of methyl 4-methylbenzoate: hydride addition to the ester, loss of methoxide to 4-methylbenzaldehyde, a second hydride from a fresh aluminate, and the water workup that gives (4-methylphenyl)methanol and methanol.
- Sharpless AD of (E)-dec-5-ene to (5R,6R)-decane-5,6-diolDraw the Sharpless asymmetric dihydroxylation of (E)-dec-5-ene with AD-mix-β: the [3+2] cycloaddition of OsO4 on one face and the two hydrolysis steps that release (5R,6R)-decane-5,6-diol.
- Sharpless AD of styrene to (R)-1-phenylethane-1,2-diolDraw the ligand-accelerated [3+2] addition of OsO4 to one face of styrene and the hydrolysis of the osmate ester, and explain how AD-mix-β gives (R)-1-phenylethane-1,2-diol.
- Swern oxidation of 3-phenylpropan-1-ol to 3-phenylpropanalDraw the Swern oxidation of 3-phenylpropan-1-ol: DMSO activated by oxalyl chloride, fragmentation to the chlorodimethylsulfonium ion, the alkoxysulfonium ion, ylide formation with triethylamine and the elimination that gives 3-phenylpropanal.
- TEMPO/bleach oxidation of pentan-1-ol to pentanalDraw addition of pentan-1-ol to the nitrogen of the oxoammonium ion formed from TEMPO, deprotonation by hypochlorite, and the intramolecular elimination that gives pentanal and the hydroxylamine.
- Upjohn dihydroxylation of cis-cycloocteneDraw the [3+2] addition of OsO4 to cis-cyclooctene and the hydrolysis of the cyclic osmate ester that delivers meso cis-cyclooctane-1,2-diol, explaining why NMO lets osmium be catalytic.
- Wacker oxidation of oct-1-ene to octan-2-oneDraw the palladium(II)-promoted Markovnikov attack of water on oct-1-ene, the β-hydride elimination and loss of HCl that release Pd(0), and the tautomerisation of the enol to octan-2-one.
- Wolff–Kishner reduction of acetophenone to ethylbenzeneDraw hydrazone formation from acetophenone under basic conditions, then the N–H deprotonations, carbon protonations by water and loss of N2 that turn the C=O carbon into the CH2 group of ethylbenzene.
- Wolff–Kishner reduction of cyclopentanone to cyclopentaneDraw hydrazone formation from cyclopentanone in hot basic ethylene glycol, then the deprotonations, carbon protonations and loss of N2 that turn the ring C=O into a CH2 group of cyclopentane.
Predict the product 15
- Baeyer–Villiger on Acetophenone: Which Ester?Predict the ester from a Baeyer–Villiger oxidation using migratory aptitude.
- Birch Reduction of Toluene: Pick the DienePredict the regiochemistry of the Birch reduction of an arene with an electron-donating group.
- NaBH4 on a Keto Ester: Methyl 4-OxocyclohexanecarboxylatePredict which carbonyl NaBH4 reduces in a molecule with both a ketone and an ester.
- Product of DIBAL-H and methyl hexanoate at −78 °CPredict the product of reducing methyl hexanoate with one equivalent of DIBAL-H at −78 °C followed by aqueous workup.
- H2, Pd/C on Hex-5-en-2-one: Which Group Reduces?Predict the product when an unconjugated enone is hydrogenated over palladium.
- H2, Pd/C on Benzyl Cyclohexyl EtherPredict the products when a benzyl ether protecting group is removed by hydrogenolysis.
- Product of LiAlH4 and N,N-dimethylbenzamidePredict the product of reducing a tertiary benzamide, N,N-dimethylbenzamide, with excess LiAlH4 followed by aqueous workup.
- Product of LiAlH4 and benzonitrilePredict the product of reducing benzonitrile with excess LiAlH4 followed by aqueous workup.
- Lindlar Reduction of Hex-3-yne: Predict the AlkenePredict the alkene geometry formed when an internal alkyne is hydrogenated over Lindlar catalyst.
- Na in NH3 on Hex-3-yne: Predict the AlkenePredict the alkene geometry when an internal alkyne is reduced by sodium in liquid ammonia.
- Hydrogenating Nitrobenzene Over Pd/CPredict the product of catalytic hydrogenation of a nitroarene.
- Oxidize a secondary alcoholPredict the product of Jones oxidation of a secondary alcohol (hexan-2-ol).
- PCC and a tertiary alcoholPredict what PCC does to a tertiary alcohol (2-methylbutan-2-ol).
- O3 Then H2O2 on Cyclohexene: Predict the ProductPredict the product of ozonolysis with oxidative workup.
- O3 Then Me2S on Cyclohexene: Pick the ProductPredict the product of reductive ozonolysis of a cyclic alkene.
Classify 7
- Rank carbon oxidation levelsClassify two-carbon compounds by the oxidation level of the functionalised carbon.
- Which functional groups does LiAlH4 reduce?Classify functional groups by whether lithium aluminium hydride reduces them: polar π bonds and strained C–O bonds versus isolated C=C, arenes and ethers.
- Which carbonyl groups does NaBH4 reduce?Classify carbonyl groups by whether sodium borohydride in methanol reduces them, using carbonyl electrophilicity.
- Ox, red or neither?Classify a functional-group change as oxidation, reduction or neither by counting C–H and C–heteroatom bonds.
- Ester versus acid oxidation levelDecide whether converting a carboxylic acid into an ester changes the oxidation level of carbon.
- Tollens' testUse Tollens' reagent to tell an aldehyde from a ketone.
- Wolff–Kishner Reduction: Identify the ReagentsIdentify the reagent set used for a Wolff–Kishner reduction.
Compare 5
- NaBH4 or LiAlH4 on ethyl 3-oxobutanoateCompare which carbonyls of a keto ester NaBH4 and LiAlH4 each reduce.
- Alkene or Ketone: H2/Pd vs NaBH4 on a Cyclohexenyl KetoneMatch each reducing agent to the functional group it reduces selectively.
- Rank Hydride Donors: LiAlH4 to NaBH3CNOrder common hydride reagents by how strongly they donate hydride to a carbonyl group.
- Cold vs Hot KMnO4 on CyclohexeneCompare the products of permanganate oxidation of an alkene under cold and hot conditions.
- Oxidation ladderOrder one- and two-carbon compounds by the oxidation level of carbon.
Calculate 3
- Moles of LiAlH4 for Ethyl BenzoateCalculate the minimum amount of LiAlH4 needed to reduce an ester to a primary alcohol.
- Oxidation state of a carbonyl carbonCalculate the oxidation state of the carbonyl carbon in acetaldehyde.
- Electrons Lost: Propan-2-ol to AcetoneCalculate the number of electrons lost by carbon when a secondary alcohol is oxidised to a ketone.
Find the error 1
- A borohydride answer that reduced an esterDiagnose an answer in which NaBH4 is drawn reducing a simple ester.
Interpret the evidence 1
- Swern byproductsIdentify the byproducts of a Swern oxidation and the source of its smell.
Work backward 1
- Which ester gives butan-1-ol and ethanolWork backwards from the two alcohols of an ester reduction to the ester that produced them.
Plan a synthesis 7
- Stop hexan-1-ol at the aldehydePlan an oxidation that converts a primary alcohol into the aldehyde without over-oxidation.
- 4-Nitroacetophenone to 4-AminoacetophenoneChoose a reagent that reduces an aromatic nitro group without touching a ketone.
- Deoxygenate a Ketone That Carries an AcetalChoose between Clemmensen and Wolff–Kishner reduction based on a substrate's acid or base sensitivity.
- Benzoyl Chloride to Benzaldehyde: Pick the HydrideChoose a hydride reagent that reduces an acid chloride only as far as the aldehyde.
- Go all the way to the acidChoose an oxidant that converts a primary alcohol into a carboxylic acid.
- Stop at the aldehydeChoose an oxidant that converts a primary alcohol into an aldehyde without over-oxidation.
- Rosenmund Reduction: Butanoyl Chloride to ButanalChoose catalytic hydrogenation conditions that turn an acyl chloride into an aldehyde.
Explain why 1
- Why LiAlH4 does not stop at the aldehydeExplain why lithium aluminium hydride reduces an ester past the aldehyde stage.
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