NCEA Level 3 Organic Chemistry Reaction Schemes Practice Test

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• In a Claisen-Schmidt condensation between benzaldehyde and acetophenone, what is the product?
• In concentrated acid, tert-butyl bromide undergoes which mechanism and what is the major product?
• In electrophilic aromatic substitution, which statement about the mechanism is true?
• Ethyl benzoate plus ammonia under heating gives which product?
• Which reagent hydrates an alkene to form an alcohol?
• Which reagents form a secondary amide in the scheme?
• Reduction of acetone with NaBH4 yields which product?
• Which reagent is used to form the cyanohydrin from acetaldehyde?
• Acid hydrolysis of an ester yields which products?
• Reduction of benzaldehyde with NaBH4 gives which product?
• Which reagent converts a carboxylic acid to a carboxylate salt?
• An ester reacts with ammonia in ethanol. Which products form?
• In an SN2 reaction, ethyl bromide treated with cyanide yields which nitrile?
• Fischer esterification of benzoic acid with ethanol yields which compound?
• Hydration of propene with dilute sulfuric acid gives which product and which rule governs regiochemistry?
• Which reagents convert an acid chloride to a primary amide?
• Hydrolyze ethyl benzoate under acidic conditions. What is the product?
• Which reagents convert an acid chloride to an ester?
• Under basic conditions, acetaldehyde undergoes an aldol condensation with itself. What is the major dehydrated product?
• Base hydrolysis of an amide yields which nitrogen-containing product?
• Reduction with NaBH4 or LiAlH4 of a ketone yields which product?
• Which main product results from reducing ethyl benzoate with LiAlH4?
• From the self-condensation of acetaldehyde under basic aldol conditions, which compound is formed by dehydration of the aldol product?
• In an SN1 reaction, tert-butyl bromide treated in water yields which product?
• Which reagents form a carboxylate salt from a carboxylic acid?
• Lindlar-catalyzed hydrogenation of phenylacetylene produces which product?
• Which reagents form an ester from an acid chloride?
• Oxidation of a benzylic secondary alcohol typically yields which product?
• Why does SN1 often lead to racemic products when starting from a chiral center?
• What are the general products of a Grignard reaction with water, alcohols, or other proton sources?
• What is the key difference between PCC and Jones oxidation for primary alcohols?
• Which reagent converts Alcohol to Haloalkane under reflux?
• What is the role of Cr2O7^2-/H+ in the oxidation steps described?
• Benzaldehyde with phenylhydrazine yields which type of product?
• What is the product when an alkene is treated with Br2?
• Grignard reagent methylmagnesium bromide added to benzaldehyde gives which alcohol after workup?
• Which reducing agent reduces esters to alcohols?
• Hydrolysis of an amide under acidic conditions yields which two products?
• Catalytic hydrogenation of cyclohexene with H2/Pt gives what product?
• Predict the major product of the hydrogenation of 1-hexyne with a Lindlar catalyst.
• Acidic hydrolysis of acetonitrile yields which acid?
• Oxidation of a primary alcohol using Jones oxidation yields which product?
• In SN2, if the substrate is chiral, what is the typical stereochemical outcome?
• Hydration of propyne (1-propyne) with HgSO4/H2SO4 yields which ketone?
• The reaction of an acyl chloride with aniline yields which functional group?
• Nitrobenzene subjected to catalytic hydrogenation over Pd/C yields which compound?
• What is the mechanism and major product when benzyl chloride reacts with water under acidic conditions?
• Electrophilic aromatic sulfonation of benzene gives which major product?
• Under basic aldol condensation of acetaldehyde, the aldol product can dehydrate to which compound?
• Grignard reaction of an aldehyde (R'CHO) with RMgX yields on workup?
• What happens when a haloalkane is treated with aqueous KOH under reflux?
• A haloalkane is converted to an alcohol under reflux using which reagents?
• Nitrobenzene is reduced to aniline by what reagents?
• Saponification of ethyl acetate in base yields which salt?
• Hydrogenate ethyl acrylate (CH2=CH-CO2Et) with H2/Pd. What is the major product?
• Reduction with NaBH4 or LiAlH4 of an aldehyde yields which product?
• Knoevenagel condensation between benzaldehyde and malononitrile yields which product?
• Oxidation of a secondary alcohol with Cr2O7^2-/H+ under reflux yields which product?
• Under hot, concentrated KMnO4, alkenes undergo oxidative cleavage to yield which products?
• Nitration of benzene with conc. HNO3/H2SO4 gives what product?
• In SN2 displacement of ethyl bromide by cyanide, which nitrile is formed?
• Alkene hydrogenated with H2 and a nickel catalyst at heat yields which product?
• Nitration of toluene typically yields which major product?
• What is the product when an alkane is treated with X2 under UV light (slow reaction)?
• Which reagent is commonly used to reduce nitrobenzene to aniline?
• Which reagent converts a Haloalkane to an Aminoalkane?
• Jones oxidation of ethanol yields which product?
• Catalytic hydrogenation of cyclohexene gives which product?
• A Wittig reaction between benzaldehyde and methylidenetriphenylphosphorane yields which product?
• Amide hydrolysis under basic conditions yields which products?
• Which reagent acts as the Lewis acid catalyst in the Friedel–Crafts reactions described?
• Which reagents convert a carboxylic acid to the corresponding acid chloride?
• During dehydration of a tertiary alcohol under concentrated acid, which mechanism is typical and what is the major product type?
• Fischer esterification on benzoic acid with ethanol yields which product?
• Friedel–Crafts acylation product name: In the acylation of benzene with acetyl chloride in AlCl3, what is the IUPAC name of the ketone product?
• What solvent is used in the SN2 reaction of an alkyl bromide with cyanide in the described example?
• Friedel–Crafts acylation of benzene with acetyl chloride and AlCl3 yields which product?
• Protection of an alcohol with tert-butyldimethylsilyl chloride yields which protecting group?
• Which reagent converts a carboxylic acid to an acid chloride?
• The aldol condensation self-reaction of acetaldehyde yields which aldol product?
• Which reagent converts an alcohol to a tosylate, improving its leaving group for substitution?
• Esters are formed from carboxylic acids and alcohols in the presence of conc. sulfuric acid. Which statement correctly describes this esterification?
• Imine formation from benzaldehyde and aniline yields what kind of intermediate?
• Oxidation of a primary alcohol with Cr2O7^2-/H+ under reflux yields which product?
• Oxidation of a secondary alcohol with PCC yields what?
• Conversion of a carboxylic acid to an acid chloride uses which reagent?
• Which statement best describes hydroboration-oxidation of propene?
• Which reagents are used for the Fischer esterification in the scheme?
• Which reagents would produce an ester directly from an acid chloride in the scheme?
• Under Cr2O7^2-/H+ reflux, oxidation of a secondary alcohol produces which product?
• Grignard reaction of acetone with methylmagnesium bromide yields after hydrolysis?
• Predict the product of dehydration of 2-methyl-2-butanol with concentrated sulfuric acid.
• Which is the Knoevenagel condensation product between benzaldehyde and malononitrile?
• Which products are formed when a haloalkane undergoes dehydrohalogenation with a base?
• Treating an alkene with cold, dilute KMnO4 yields which product?
• What is the product of reducing benzaldehyde with NaBH4?
• Imine formation from benzaldehyde and aniline yields an imine functional group with which linkage?
• Oxidation with Cr2O7^2-/H+ reflux of an aldehyde yields which product?
• During the nitration of benzene, what is the major product?
• Grignard reaction with formaldehyde followed by acid workup yields what type of product?
• Base hydrolysis (saponification) of an ester with dilute NaOH yields which pair of products?
• In a Williamson ether synthesis, which substrate is most suitable for SN2 to form the ether?
• Grignard reaction of methylmagnesium bromide with CO2 gives which carboxylic acid after workup?
• For a primary alkyl chloride in water, which mechanism dominates and what is the likely product?
• Which reagent is used for base hydrolysis of esters?
• Alkene hydrated with water under acidic conditions yields which product?
• A bulky base in E2 reactions tends to favor which product?
• What happens when a haloalkane is treated with alcoholic KOH under reflux?
• During saponification of an ester with base, which two products are formed before any acid workup?
• In acid-catalyzed hydration of an asymmetrical alkene, the hydroxyl group adds to which carbon in the major product?
• In the nitration of anisole, which product is formed as the major product?
• In base hydrolysis of an ester, which product is formed?
• Which condition would convert a Haloalkane to an Alkene?
• When a haloalkane is subjected to X2 under UV light, what products are formed?
• Grignard addition to formaldehyde using phenylmagnesium bromide yields which product after workup?
• Amide hydrolysis under acidic conditions yields what?
• An alkene is hydrated with conc sulfuric acid to form which product?
• In the reaction of ethyl benzoate with ammonia under heating, what byproduct is formed alongside the major amide product?
• PCC oxidation of 2-propanol yields which product?
• Which reagents convert an acid chloride to a secondary amide?
• Which class of compound is produced when benzaldehyde reacts with phenylhydrazine?
• Which reagent would you use to reduce an aldehyde to a primary alcohol?
• Tosylation of an alcohol produces a what kind of leaving group?
• Exhaustive hydrogenation of 1-hexyne with hydrogen and a poisoned catalyst gives which product?
• When methyl iodide reacts with sodium hydroxide in water, what is the mechanism and product?
• Ester reacted with ammonia in ethanol yields which pair of products?
• Which set of reagents is used to form an ester from an alcohol and a carboxylic acid under acidic conditions?
• Which reagents form a primary amide in the scheme?
• What catalyst is typically used for Fischer esterification of a carboxylic acid with methanol?
• Reduction of benzoic acid with LiAlH4 yields which product?
• Hydrogenation of alkenes using H2 and Ni yields which product?
• What is the outcome when tert-butyl bromide reacts with water under heat?
• Reaction of an aldehyde with hydroxylamine produces which type of compound?
• Hydrogenation of an alkyne with a poisoned catalyst yields which product?
• Acid-catalyzed hydration of propene yields which alcohol?
• In electrophilic nitration of anisole, which nitrated product is major?
• Halohydrin formation from propene with Br2/H2O yields which product?
• NaBH4 reduces acetophenone to which product?
• A common product of esterification of a carboxylic acid with methanol under acid catalysis is what?
• Refluxing an alcohol with SOCl2 or PCl3 or PCl5 converts it to what?
• In aqueous acid, what is the mechanism and major product for the reaction of 2-bromopentane?
• In the nitration of toluene, besides the major para product, which other nitro product is formed in smaller amounts?
• Amide formation from a carboxylic acid derivative and ammonia yields which product?
• Which reagent(s) can convert an Alcohol to a Haloalkane under reflux?
• Which reaction sequence adds water to an alkene in Markovnikov fashion without carbocation rearrangement?
• Which statement describes saponification of esters?
• Alkene treated with bromine (Br2) yields which product?
• Dehydration of tert-butyl bromide in concentrated acid yields which major alkene?
• Jones oxidation of benzyl alcohol yields which product?
• What is the product when an alkene is hydrogenated with H2 in the presence of Ni or Pt and heat?
• Reaction of an alkene with HX yields which product?
• An aminoalkane heated with ammonia yields which product?
• In the presence of peroxides, hydrohalogenation of asymmetrical alkenes proceeds with what regiochemistry?
• Which product characterizes the mild oxidation of alkenes with KMnO4?
• Amide formation: acyl chloride + aniline yields which product?
• Cyanohydrin formation: acetaldehyde with HCN yields which product?
• What reagent is commonly used to dehydrate an Alcohol to form an Alkene?
• Reaction of a ketone with hydroxylamine yields which type of compound?
• Jones oxidation uses chromium trioxide in acetone. Which statement about this reagent is true?
• Reaction of an acid chloride with water yields which product?
• In SN1 reactions, what dictates whether rearrangements occur?
• Transesterification of ethyl benzoate with methanol under acid catalysis yields which ester?
• In SN1 reactions, which step is rate-determining?
• An acid chloride treated with ammonia in ethanol yields which product?
• Enamine formation: acetone reacts with dimethylamine. What is the product?
• What is the major alkene produced from dehydrohalogenation of 1-bromo-2-methylpropane with a strong base?
• Which statement correctly describes the oxidation of secondary alcohols by PCC and Jones?
• Jones oxidation of ethanol yields which product?
• Oxidation of a secondary alcohol yields which type of compound?
• An acid chloride treated with a primary amine yields which product?
• Friedel–Crafts alkylation of benzene with tert-butyl chloride yields which major product?
• What is the product when an alkene is treated with water under acidic conditions (H2O/H+ and heat)?
• For CH3CH2CH2Br reacting with NaCN in DMF, which mechanism occurs and what is the major product?
• Which product results from the hydrogenation of cyclohexene?
• Grignard reaction with CO2 followed by acid workup yields what?
• Under Cr2O7^2-/H+ reflux, oxidation of a primary alcohol yields which product?
• In the aldol reaction of acetaldehyde under basic conditions, which species acts as electrophile?
• Base hydrolysis of an amide yields which pair of products?
• In the scheme, a secondary alcohol is shown to form what product with the listed reagents?
• Oxidation of 1-phenylethaneol yields which product?
• In the scheme, a primary alcohol is shown to form what product and reagents?
• Under basic conditions, acetaldehyde self-aldol condensates; which is the major dehydrated product?
• Which reagent can reduce both aldehydes and ketones?
• Under acid hydrolysis, which description matches the ester hydrolysis in the scheme?
• In Fischer esterification, which catalyst is commonly used?
• In a Williamson ether synthesis, which combination is needed to form an ether under SN2 conditions?
• Which reagent is used to perform base hydrolysis of esters (saponification)?
• What reagents are used to nitrate benzene?
• Hydrolysis of an acid chloride with water yields carboxylic acid and which byproduct?
• At low temperature, DIBAL-H reduces ethyl benzoate to which product?
• Which product is formed when CO2 is treated with methylmagnesium bromide followed by acidic workup?
• Which product results from the Wittig reaction of benzaldehyde with methylidenetriphenylphosphorane?
• Fischer esterification involves which two species and what is the general product?
• Formation of an imine from acetaldehyde and aniline. What is the imine functional group called in this product?
• Predict the product when benzyl alcohol is oxidized with PCC in dichloromethane, followed by aqueous workup.
• Which class of compound is cinnamaldehyde, produced by the cross-aldol reaction between benzaldehyde and acetaldehyde followed by dehydration?
• Ester hydrolysis (saponification) with NaOH followed by acid workup yields what species initially?
• Grignard reagent encountering water: what are the products?
• An acid chloride treated with a secondary amine yields which product?
• Which reagent is used to convert a haloalkane to an alcohol under reflux?
• To selectively obtain an aldehyde from a primary alcohol oxidation with dichromate, which technique is employed?
• In an aldol reaction, which condition favors self-condensation of acetaldehyde to give 3-hydroxybutanal?
• An ester reacts with ammonia in alcohol to form which products?
• Which reagent is commonly used to convert an alcohol to an alkyl chloride?
• Electrophilic aromatic sulfonation of benzene yields which product?
• Under mild oxidation with KMnO4, which product is expected from an alkene?
• Concentrated sulfuric acid (cH2SO4) promotes dehydration of an Alcohol to form which product?
• Aldehyde + ethylene glycol under acid catalysis forms what type of protecting group?
• Benzoyl chloride reacts with ammonia to yield which major product?
• Aldehyde + ethylene glycol forms which protecting group?
• Under Cr2O7^2-/H+ distillation, oxidation of a primary alcohol yields which product?
• Diels–Alder reaction between butadiene and ethene yields which ring system?
• Grignard reaction of methylmagnesium bromide with benzaldehyde yields which alcohol after workup?
• What are the products when a carboxylic acid is treated with ammonia solution?
• Oxymercuration-demercuration of propene yields which product and why is it special?
• Elimination vs substitution: 2-bromopropane treated with sodium ethoxide in ethanol yields what major product?
• Base hydrolysis of an ester in aqueous solution yields which products?
• Which reagent oxidizes a secondary alcohol to a ketone?
• Which statement is true about oxidation of secondary alcohols with common oxidants?
• Self-condensation (Claisen) of ethyl acetate under base yields which β-keto ester?
• Which oxidant selectively stops at an aldehyde when oxidizing a primary alcohol?
• Which reagents convert an acid chloride to a carboxylic acid?
• Cross-aldol reaction between benzaldehyde and acetaldehyde under base yields which α,β-unsaturated aldehyde after dehydration?
• In a typical Diels–Alder reaction, which component acts as the dienophile?
• Hydration of a terminal alkyne 1-hexyne using HgSO4/H2SO4 gives what carbonyl compound?
• Hydroboration-oxidation of propene yields which product, and what is the regioselectivity?
• Nitration of anisole gives mainly which product and why?
• Oxidation of a primary alcohol using PCC in suitable solvent yields which product?
• An alcohol is heated with aqueous KOH under reflux. What is the product?
• Which statement correctly describes Grignard reagents reacting with proton sources?
• For 2-bromobutane treated with KOH in ethanol, which is the major elimination product and which is the minor product?
• NH3 warm on a haloalkane yields which product?
• Amide hydrolysis: acetamide under acidic conditions yields which products?
• Reduction of an ester with LiAlH4 yields what type of product?
• Which protecting group is formed when an aldehyde reacts with ethylene glycol?
• Which reducing agent reduces ethyl benzoate to benzyl alcohol?
• In Friedel–Crafts acylation of benzene with acetyl chloride, which species acts as the actual electrophile that attacks the ring?
• Among the following statements, which accurately describes reducing esters?
• An alkene treated with alcoholic potassium hydroxide under reflux yields which compound?
• Which oxidizing agent is used to oxidize 2-propanol to acetone in the example given?
• In toluene nitration, which positions are favored and why?
• Which combination is used to convert a carboxylic acid to an ester?
• Which substrate would form a resonance-stabilized carbocation intermediate under SN1 conditions?
• Which reagent converts an aldehyde to its oxime?
• Addition of Br2 to alkenes yields which type of product?
• An acid chloride treated with a tertiary amine yields which product?
• Base hydrolysis of an amide yields which products?
• In base hydrolysis of an amide, the nitrogen-containing product is which?
• Reaction of a ketone with hydroxylamine yields which type of compound?
• Jones oxidation of benzyl alcohol yields which product?
• Oxidation of a primary alcohol with Cr2O7^2-/H+ under distillation yields which product?
• Which oxidation method fully oxidizes primary alcohols to carboxylic acids?
• Friedel–Crafts acylation of benzene with acetyl chloride in AlCl3 gives which ketone?