Organic Chemistry 2 · Carbonyl and enolate chemistry
Enols, enolates and alpha reactions: practice problems
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- α-Bromination of acetophenone to phenacyl bromide
- Hell–Volhard–Zelinsky bromination of propanoic acid to 2-bromopropanoic acid
- Iodoform reaction of acetone to acetate and iodoform
- α-Methylation of cyclohexanone to 2-methylcyclohexanone
- 2-Methylcyclohexanone by Stork enamine methylation of cyclohexanone
- Track alpha deprotonation
- Use the carbon-centered enolate contributor
- Make an enol without a strong base
- Haloform reaction — acetophenone bromination and cleavage
Draw the mechanism 84
- Track alpha deprotonationDraw all three electron-pair movements that generate an oxygen-centered enolate contributor.
- Use the carbon-centered enolate contributorDraw SN2 alpha alkylation and track the leaving-group charge.
- Make an enol without a strong baseDistinguish acid-catalyzed enolization from formation of an anionic enolate.
- Haloform reaction — acetophenone bromination and cleavageExecute all three alpha brominations, nucleophilic acyl cleavage and the final proton transfer.
- A base converts an enol to a ketoneSeparate oxygen deprotonation, enolate resonance and carbon protonation.
- Exchange an alpha hydrogen with heavy waterFollow the isotopes through reversible enolate formation and carbon reprotonation.
- Trap a designated kinetic enolateCombine regioselective strong-base deprotonation with complete C-alkylation rather than starting with an isolated carbanion.
- Malonic ester synthesis — malonate allylation stageUse the doubly stabilized methylene and retain the remote alkene during monoalkylation.
- A carbon nucleophile closes a ketone ringCount a six-membered ring in intramolecular enolate alkylation and distinguish it from aldol addition.
- Trap an enolate at oxygenRecognize an O-trapping electrophile and preserve the enolate carbon–carbon double bond.
- An epoxide extends an ester side chainUse ring-opening C-alkylation to install a two-carbon alcohol fragment.
- An enol encounters molecular bromineComplete catalytic enolization and electrophilic alpha bromination with the new acid equivalent retained.
- Deprotonate between two carbonylsExplain the high acidity of a 1,3-dicarbonyl compound by generating all three contributors of its conjugate base.
- Ethyl 2-ethyl-2-methyl-3-oxobutanoate by two alkylations of ethyl acetoacetateDraw two rounds of ethoxide deprotonation and SN2 alkylation at the carbon between the two carbonyls of ethyl acetoacetate, first with methyl iodide and then with ethyl bromide.
- Ethyl 3-oxooctanoate by γ-alkylation of the ethyl acetoacetate dianionForm the dianion of ethyl acetoacetate with two equivalents of LDA, alkylate it at the terminal (γ) carbon with 1-bromobutane, and protonate the remaining enolate.
- 3-Methylpentane-2,4-dione from pentane-2,4-dione and methyl iodideUse carbonate to deprotonate pentane-2,4-dione between its carbonyls and draw the SN2 methylation of the resulting enolate carbon.
- Acid α-bromination of 2-methylcyclohexanone at C2Draw acetic acid protonating 2-methylcyclohexanone, the tetrasubstituted enol forming, and its attack on Br2 that gives 2-bromo-2-methylcyclohexan-1-one.
- α-Bromination of acetophenone to phenacyl bromideDraw acid-catalysed enolization of acetophenone, attack of the enol on Br2, and deprotonation to give 2-bromo-1-phenylethan-1-one.
- Acid α-bromination of butan-2-one at C3Draw HBr protonating butan-2-one, acetic acid forming the more substituted enol, and that enol attacking Br2 at C3 to give 3-bromobutan-2-one.
- Acid-catalysed α-chlorination of cyclohexanone to 2-chlorocyclohexanoneDraw acid-catalysed enol formation from cyclohexanone, attack of the enol on Cl2, and loss of the O–H proton to give 2-chlorocyclohexanone.
- Cyclohex-1-en-1-ol from cyclohexanone in aqueous acidDraw acid-catalysed enolization of cyclohexanone: protonation of the carbonyl oxygen, then loss of an α-hydrogen to water (cyclohexanone).
- Acid-catalysed racemization of 3-phenylbutan-2-oneDraw protonation of the carbonyl, loss of the α-hydrogen to form the planar enol, reprotonation of the enol carbon, and deprotonation of oxygen, showing why the stereocentre is lost.
- 3-Phenylpropanal by aza-enolate benzylationDraw LDA forming the aza-enolate of N-ethylidenecyclohexanamine, its SN2 benzylation and acid hydrolysis of the imine to 3-phenylpropanal.
- Base-promoted α,α-dibromination of propiophenoneDraw two rounds of hydroxide deprotonation and enolate bromination at the same α-carbon of propiophenone, giving 2,2-dibromo-1-phenylpropan-1-one.
- Base-catalysed racemization of 3-phenylbutan-2-oneDraw ethoxide removing the α-hydrogen on the stereocentre, the carbanion contributor of the planar enolate, and reprotonation by ethanol, showing why the ketone racemizes.
- Bromoform cleavage of ethyl levulinate, ester intactDraw the three enolate brominations of the methyl ketone of ethyl levulinate, hydroxide addition and loss of the tribromomethyl anion that give 4-ethoxy-4-oxobutanoate and bromoform.
- Dehydrobromination of 2-bromocyclohexanone to cyclohex-2-en-1-oneDraw the one-step E2 in which pyridine removes the C3 hydrogen of 2-bromocyclohexanone as bromide leaves, giving cyclohex-2-en-1-one.
- Cyclopropyl methyl ketone from 5-chloropentan-2-oneDraw hydroxide forming the C3 enolate of 5-chloropentan-2-one and the intramolecular SN2 that closes the three-membered ring of 1-cyclopropylethan-1-one.
- C-Methylation of cyclohexane-1,3-dione with KOH and MeIDraw hydroxide removing the C2 hydrogen between the two carbonyls of cyclohexane-1,3-dione and the enolate carbon attacking methyl iodide to give 2-methylcyclohexane-1,3-dione.
- 2-Butyl-2-methyl-1,3-dithiane by dithiane alkylationDraw n-butyllithium deprotonating 2-methyl-1,3-dithiane at C2 and the dithiane anion alkylating 1-bromobutane.
- Phenyl(1,3-dithian-2-yl)methanol by dithiane additionDraw lithiation of 1,3-dithiane, addition of the dithiane anion to benzaldehyde and protonation to phenyl(1,3-dithian-2-yl)methanol.
- 1-(1,3-Dithian-2-yl)propan-2-ol from propylene oxideDraw lithiation of 1,3-dithiane and SN2 opening of propylene oxide at its less hindered carbon to give 1-(1,3-dithian-2-yl)propan-2-ol.
- 2-Allyl-6-methylcyclohexanone by enamine allylationDraw allylation of the 2-methylcyclohexanone pyrrolidine enamine at its less substituted carbon and hydrolysis to 2-allyl-6-methylcyclohexanone.
- 2-Oxocyclohexane-1-carboxylic acid from the cyclohexanone enolate and CO2Form the lithium enolate of cyclohexanone, add its α-carbon to carbon dioxide, and protonate the carboxylate to the β-keto acid.
- 2-(2-Hydroxyethyl)cyclohexan-1-one by enolate opening of ethylene oxideForm the cyclohexanone enolate with LDA, draw its SN2 attack on ethylene oxide, and protonate the alkoxide to 2-(2-hydroxyethyl)cyclohexan-1-one.
- Epimerizing trans-4-tert-butyl-2-methylcyclohexanoneDraw methoxide forming the enolate of trans-4-tert-butyl-2-methylcyclohexanone and methanol reprotonating it to the more stable cis isomer.
- Ethyl 2,2,2-trideuterioacetate by α-H/D exchangeDraw three rounds of ethoxide deprotonation and O-deuterated ethanol deuteration that exchange every α-hydrogen of ethyl acetate for deuterium.
- Methyl cyclopentanecarboxylate by Favorskii ring contraction of 2-chlorocyclohexanoneDraw the Favorskii ring contraction: α′-enolate, cyclopropanone formation by displacement of chloride, methoxide addition, ring opening and protonation to methyl cyclopentanecarboxylate.
- Haloform reaction of pinacolone to pivalate and bromoformDraw the three enolate brominations of pinacolone, hydroxide addition to the carbonyl and loss of the tribromomethyl anion that give pivalate and bromoform.
- Benzaldehyde by Hass–Bender oxidation of benzyl bromideDraw the 2-nitropropane nitronate alkylating benzyl bromide on oxygen and the nitronic ester fragmenting to benzaldehyde and acetone oxime.
- HVZ of 3-methylbutanoic acid with an ethanol quenchDraw the HVZ bromination of 3-methylbutanoic acid through its acyl bromide enol and the ethanol quench that converts the α-bromo acyl bromide into ethyl 2-bromo-3-methylbutanoate.
- Hell–Volhard–Zelinsky bromination of phenylacetic acidDraw PBr3 converting phenylacetic acid into its acyl bromide, enolization and α-bromination, and hydrolysis by water that gives 2-bromo-2-phenylacetic acid.
- Hell–Volhard–Zelinsky bromination of propanoic acid to 2-bromopropanoic acidDraw conversion of propanoic acid to propanoyl bromide with PBr3, enolization and α-bromination of the acyl bromide, and hydrolysis to 2-bromopropanoic acid.
- Iodoform reaction of acetone to acetate and iodoformDraw three cycles of enolate formation and iodination at one methyl of acetone, hydroxide addition to the carbonyl, loss of the triiodomethyl anion, and the final proton transfer giving acetate and iodoform.
- Iodoform test on cyclohexyl methyl ketoneDraw the three enolate iodinations of cyclohexyl methyl ketone and the hydroxide cleavage that releases cyclohexanecarboxylate and iodoform.
- Quaternary nitrile from isobutyronitrile benzylationDraw LDA deprotonating isobutyronitrile and the tertiary nitrile anion benzylating to give the quaternary 2,2-dimethyl-3-phenylpropanenitrile.
- Kinetic methylation of 2-methylcyclohexanone to 2,6-dimethylcyclohexanoneDraw LDA forming the less substituted (kinetic) enolate of 2-methylcyclohexanone, its carbanion contributor, and methylation at C6 to give 2,6-dimethylcyclohexanone.
- Kinetic methylation of 3-methylcyclohexanoneDraw bulky LDA removing a C6 hydrogen of 3-methylcyclohexanone and the resulting enolate attacking methyl iodide to give 2,5-dimethylcyclohexan-1-one.
- Kinetic benzylation of butan-2-one to 1-phenylpentan-3-oneDraw LDA removing a methyl hydrogen of butan-2-one, the kinetic enolate, and SN2 attack on benzyl bromide that gives 1-phenylpentan-3-one.
- Kinetic enol acetate of 2-methylcyclohexanoneDraw LDA forming the kinetic enolate of 2-methylcyclohexanone and the enolate oxygen acylated by acetic anhydride to give the less substituted enol acetate.
- Kinetic TMS enol ether of 2-methylcyclopentanoneDraw LDA forming the kinetic enolate of 2-methylcyclopentanone and the enolate oxygen attacking chlorotrimethylsilane to give trimethyl((5-methylcyclopent-1-en-1-yl)oxy)silane.
- Kinetic trimethylsilyl enol ether of 2-methylcyclohexanoneDraw LDA forming the kinetic enolate of 2-methylcyclohexanone and the enolate oxygen attacking chlorotrimethylsilane to trap it as the less substituted silyl enol ether.
- Allylation of acetone to hex-5-en-2-oneDraw LDA forming the enolate of acetone, its carbanion contributor, and SN2 attack on allyl bromide that gives hex-5-en-2-one.
- α-Methylation of γ-butyrolactone with LDA and methyl iodideDraw LDA forming the enolate of γ-butyrolactone and the α-carbon displacing iodide from methyl iodide to give 3-methyloxolan-2-one.
- α-Methylation of cyclohexanone to 2-methylcyclohexanoneDraw LDA removing an α-hydrogen of cyclohexanone, the carbanion contributor of the enolate, and SN2 attack of the α-carbon on methyl iodide to give 2-methylcyclohexanone.
- Propargylation of cyclohexanone with propargyl bromideDraw the lithium enolate of cyclohexanone forming with LDA and attacking the CH2Br carbon of propargyl bromide to give 2-(prop-2-yn-1-yl)cyclohexan-1-one.
- Benzylation of cyclopentanone to 2-benzylcyclopentanoneDraw LDA deprotonating cyclopentanone, the carbanion contributor of its enolate, and SN2 attack on benzyl bromide that gives 2-benzylcyclopentan-1-one.
- Benzylation of N,N-dimethylpropanamide via its amide enolateDraw LDA forming the enolate of N,N-dimethylpropanamide and its SN2 attack on benzyl bromide that gives N,N,2-trimethyl-3-phenylpropanamide.
- Benzylation of ethyl isobutyrate to a quaternary esterDraw LDA forming the enolate of ethyl isobutyrate and its SN2 attack on benzyl bromide that gives ethyl 2,2-dimethyl-3-phenylpropanoate.
- α-Methylation of ethyl propanoate to ethyl 2-methylpropanoateDraw LDA forming the ester enolate of ethyl propanoate, its carbanion contributor, and SN2 attack on methyl iodide to give ethyl 2-methylpropanoate.
- Methylation of methyl cyclohexanecarboxylate at C1Draw LDA removing the ring C1 hydrogen of methyl cyclohexanecarboxylate and the enolate carbon attacking methyl iodide to make methyl 1-methylcyclohexane-1-carboxylate.
- Benzylation of N-methylpyrrolidinone at C3 via its enolateDraw LDA forming the C3 enolate of 1-methylpyrrolidin-2-one and its SN2 attack on benzyl bromide that gives 3-benzyl-1-methylpyrrolidin-2-one.
- Ethylation of propiophenone to 2-methyl-1-phenylbutan-1-oneDraw LDA forming the enolate of propiophenone and its SN2 attack on ethyl iodide that gives 2-methyl-1-phenylbutan-1-one.
- Allylation of tert-butyl acetate to tert-butyl pent-4-enoateDraw LDA forming the enolate of tert-butyl acetate and its SN2 attack on allyl bromide that gives tert-butyl pent-4-enoate.
- 2-Benzoylcyclopentanone by enamine acylationDraw C-benzoylation of the morpholine enamine of cyclopentanone by addition–elimination and the hydrolysis that releases 2-benzoylcyclopentanone.
- 2-Benzylcyclopentanone via a morpholine enamineDraw C-benzylation of the morpholine enamine of cyclopentanone and hydrolysis of the iminium ion to 2-benzylcyclopentanone.
- Cyclohexanone by Nef reaction of nitrocyclohexaneDraw the nitronate of nitrocyclohexane and its acid hydrolysis through the 1-nitroso alcohol to cyclohexanone.
- 3-Phenylpropanenitrile by alkylating acetonitrile with benzyl bromideDeprotonate acetonitrile with LDA, show the ketenimine-type anion and its carbanion contributor, and draw the SN2 reaction with benzyl bromide.
- Ethanenitronate from nitroethane and hydroxideDraw hydroxide removing the α-hydrogen of nitroethane and show the charge moving onto a nitro oxygen to give the nitronate anion.
- 4-Hydroxypent-3-en-2-one, the enol of pentane-2,4-dioneDraw the acid-catalysed tautomerization of pentane-2,4-dione to its conjugated, hydrogen-bonded enol and explain why this enol dominates.
- 2-Phenylbutanenitrile by ethylating phenylacetonitrileDraw sodium amide deprotonating phenylacetonitrile and the nitrile-stabilised carbanion ethylating bromoethane to give 2-phenylbutanenitrile.
- 2-Hydroxy-6-methylcyclohexan-1-one by Rubottom oxidationDraw epoxidation of the silyl enol ether by mCPBA, acid opening of the siloxy epoxide and removal of the silyl group to give the α-hydroxy ketone.
- 2,2-Dimethylcyclohexanone from a silyl enol etherDraw methyllithium releasing the more substituted lithium enolate from a trimethylsilyl enol ether and its SN2 methylation to 2,2-dimethylcyclohexanone.
- 2-Acetylcyclohexanone by Stork enamine acylationDraw C-acylation of the cyclohexanone pyrrolidine enamine by acetyl chloride and acid hydrolysis of the iminium ion to 2-acetylcyclohexanone.
- Ethyl 2-(2-oxocyclohexyl)acetate by Stork alkylationDraw SN2 alkylation of the cyclohexanone pyrrolidine enamine by ethyl bromoacetate and hydrolysis of the iminium ion to the γ-keto ester.
- 2-Methylcyclohexanone by Stork enamine methylation of cyclohexanoneDraw enamine formation from cyclohexanone and pyrrolidine, C-methylation of the enamine with methyl iodide, and hydrolysis of the iminium ion to 2-methylcyclohexanone.
- 2-(3-Oxobutyl)cyclopentanone by Stork enamine MichaelDraw 1,4-addition of the cyclopentanone pyrrolidine enamine to methyl vinyl ketone, protonation of the enolate and hydrolysis to the 1,5-diketone.
- 2-(2-Nitro-1-phenylethyl)cyclohexanone via an enamineDraw conjugate addition of the cyclohexanone pyrrolidine enamine to β-nitrostyrene, protonation of the nitronate and hydrolysis to the γ-nitro ketone.
- Phenyl 2-phenylethyl sulfone by sulfone alkylationDraw n-butyllithium deprotonating methyl phenyl sulfone and the α-sulfonyl carbanion benzylating to phenyl 2-phenylethyl sulfone.
- Thermodynamic benzylation of 2-methylcyclohexanone to 2-benzyl-2-methylcyclohexanoneDraw tert-butoxide forming the more substituted (thermodynamic) enolate of 2-methylcyclohexanone, its carbanion contributor, and SN2 attack on benzyl bromide at C2.
- Thermodynamic methylation of 2-phenylcyclohexanoneDraw tert-butoxide forming the phenyl-conjugated enolate of 2-phenylcyclohexanone and its C2 attack on methyl iodide that gives 2-methyl-2-phenylcyclohexan-1-one.
- Thermodynamic TMS enol ether of 2-methylcyclopentanoneDraw the carbonyl oxygen of 2-methylcyclopentanone attacking chlorotrimethylsilane and triethylamine removing the C2 hydrogen to give trimethyl((2-methylcyclopent-1-en-1-yl)oxy)silane.
- Thermodynamic trimethylsilyl enol ether of 2-methylcyclohexanoneDraw the carbonyl oxygen of 2-methylcyclohexanone attacking chlorotrimethylsilane, then triethylamine removing the C2 hydrogen to give the more substituted silyl enol ether.
- trans-Selective benzylation of γ-valerolactoneDraw LDA forming the enolate of (S)-γ-valerolactone and benzyl bromide attacking the face anti to the ring methyl to give trans (3S,5S)-3-benzyl-5-methyloxolan-2-one.
Predict the product 11
- Select a rapidly trapped enolateApply kinetic control to a specified unsymmetrical ketone.
- Acetoacetic ester synthesis with 1-bromobutanePredict the methyl ketone formed by alkylation, hydrolysis and decarboxylation of ethyl acetoacetate.
- Product of cyclohexanone with Br2 in acetic acidPredict the product of acid-catalyzed α-halogenation of a ketone with one equivalent of bromine.
- α-Methylation product of ethyl propanoate with LDA and CH3IPredict the product when an ester enolate made with LDA is alkylated.
- Product of cyclohexanone with LDA, then benzyl bromidePredict the product of an LDA enolate alkylated by a reactive primary halide.
- Haloform products from acetophenone with excess Br2 and NaOHPredict the products when a methyl ketone undergoes base-promoted halogenation with excess halogen.
- HVZ product of propanoic acid with Br2 and PBr3Predict the product of Hell–Volhard–Zelinsky α-bromination of a carboxylic acid.
- Kinetic enolate of 2-methylcyclohexanone with LDAPredict which enolate a hindered strong base forms at low temperature from an unsymmetrical ketone.
- Most acidic hydrogen of ethyl acetoacetateIdentify which position of a β-keto ester is deprotonated first.
- Stork alkylation product of cyclohexanone enamine with CH3IPredict the ketone formed by alkylating an enamine and hydrolyzing the iminium ion.
- Thermodynamic enolate of 2-methylcyclohexanone with NaOEtIdentify the enolate favored when a weak alkoxide base lets the two enolates of an unsymmetrical ketone equilibrate.
Classify 5
- Decide whether a hydrogen movedDistinguish keto–enol tautomers from resonance contributors.
- Which carboxylic acid decarboxylates on gentle heating?Identify the carbonyl placement that lets a carboxylic acid lose CO2 on mild heating.
- Which compound gives a positive iodoform test?Identify the structural unit that gives a positive iodoform (haloform) test.
- Which conditions form the kinetic enolate?Recognize the base, temperature, solvent and stoichiometry that make enolate formation fast and irreversible.
- Pick the structure of LDARecognize lithium diisopropylamide and distinguish it from related strong bases.
Compare 4
- Read an equilibrating enolate mixtureDistinguish thermodynamic selection from initial deprotonation speed.
- Rank alkyl halides for enolate C-alkylationRank alkyl halides by how well they alkylate an enolate, using SN2 steric requirements.
- Hard vs soft electrophiles: O- or C-attack of an enolatePredict whether an enolate reacts through oxygen or carbon from the hardness of the electrophile.
- Rank α-acidity of four carbonyl compoundsRank carbonyl compounds by the acidity of their α-hydrogens using typical pKa values.
Calculate 7
- Estimate the extent of deprotonationApply supplied pKa values to an acid–base equilibrium.
- α-Hydrogens of benzaldehydeRecognize a carbonyl compound with no α-hydrogens.
- Count the α-hydrogens of butan-2-oneCount all hydrogens on carbons directly attached to a carbonyl carbon.
- Deuterium exchange count for 2-methylcyclohexanoneCount the hydrogens a ketone exchanges for deuterium through its enolates in basic D2O.
- log K for acetone and ethoxideUse the pKa values of the acid on each side to calculate how far a ketone is converted to its enolate.
- Maximum number of alkylations of diethyl malonateCount how many alkyl groups the central carbon of a malonic ester can receive.
- pKa of an α-hydrogen of acetoneRecall the approximate pKa of a simple ketone α-hydrogen.
Find the error 4
- Diagnose an alkylation mismatchIdentify an electrophile that cannot support ordinary SN2 enolate alkylation.
- Why methylating cyclohexanone with NaOEt overalkylatesExplain why monoalkylation of a ketone enolate can continue to dialkylation and choose conditions that prevent it.
- Deuterium exchange of 2,2,6,6-tetramethylcyclohexanoneRecognize that a ketone with fully substituted α-carbons cannot exchange hydrogens through an enolate.
- Why aqueous NaOH and CH3I fail to methylate cyclohexanoneDiagnose why a weak, nucleophilic base in water fails in a ketone alkylation.
Interpret the evidence 3
- Locate enolizable sitesIdentify alpha carbons on both sides of an unsymmetrical ketone.
- Enol content of acetoneInterpret the keto–enol equilibrium constant of a simple ketone.
- The enol of cyclohexanoneDraw the enol tautomer of a ketone.
Plan a synthesis 5
- Assess the fate of a first alkylation productRecognize that one alpha alkylation does not necessarily remove all enolizable hydrogens.
- Reagents for the pyrrolidine enamine of cyclohexanoneChoose the amine and conditions that convert a ketone into an enamine.
- Reagent to turn 2-bromocyclohexanone into cyclohexenoneChoose conditions that eliminate HBr from an α-bromo ketone to form an α,β-unsaturated ketone.
- Why LDA, not NaOEt, for cyclohexanone methylationChoose a base that converts a ketone completely into its enolate before alkylation.
- Reagent to make the silyl enol ether of cyclohexanoneChoose a reagent that traps an enolate on oxygen to give a silyl enol ether.
Explain why 9
- Track reversible alpha isotope exchangePredict the cumulative result of repeated enolization in a deuterated proton pool.
- Why base polybrominates acetone but acid stops at one BrExplain how a first α-halogen speeds base-promoted halogenation but slows acid-catalyzed halogenation.
- Acid and base both catalyze α-H/D exchange of cyclohexanoneExplain how acid and base each catalyze α-hydrogen exchange through different intermediates.
- Advantage of enamine over enolate alkylation of cyclohexanoneExplain why an enamine is a useful enolate equivalent for monoalkylating a ketone.
- Why diethyl malonate is unusually acidicExplain the acidity of a CH2 flanked by two carbonyl groups.
- Phenol: a permanent enolExplain why phenol exists as the enol rather than its keto tautomer.
- Why (R)-3-phenylbutan-2-one racemizes in baseExplain how enolate formation at an α-stereocentre destroys optical activity.
- Why pentane-2,4-dione is mostly enolExplain the factors that stabilize the enol of a 1,3-dicarbonyl compound.
- Why α-hydrogens are acidicExplain the stabilization that makes α-C–H bonds acidic.
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