DP Chemistry Questionbank

• Syllabus

Topic 20: Organic chemistry

Sub sections and their related questions

20.1 Types of organic reactions

• 15M.1.hl.TZ1.36: What should be changed to alter the rate of nucleophilic substitution of tertiary...
• 15M.1.hl.TZ2.21: The hydrolysis of tertiary bromoalkanes with a warm dilute aqueous sodium hydroxide solution...
• 15M.1.hl.TZ2.37: What is the correct order for the increasing rate of hydrolysis of halogenoalkanes by dilute...
• 15M.2.hl.TZ1.6c: Explain why the rate of the reaction between iodomethane,...
• 15M.2.hl.TZ1.7b: Ethanol can be made by reacting aqueous sodium hydroxide with bromoethane. Explain the mechanism...
• 15M.2.hl.TZ2.10c.i: Compound C, \({{\text{C}}_{\text{4}}}{{\text{H}}_{\text{9}}}{\text{OH}}\), can also be formed by...
• 15M.2.hl.TZ2.10c.ii: Explain why the hydroxide ion is a better nucleophile than water.
• 15M.1.sl.TZ2.29: Which combination best describes the substitution reaction between bromoethane and dilute aqueous...
• 14M.2.hl.TZ1.8d.i: Deduce the mechanism for the reaction using equations and curly arrows to represent the movement...
• 14M.3.hl.TZ2.27a: (i)     Identify the two reagents used to form the electrophile in the nitration of...
• 14M.1.sl.TZ1.28: Which type of halogenoalkane is the substance shown below, and which type of nucleophilic...
• 14M.1.sl.TZ2.26: In organic reaction mechanisms, what does a curly arrow represent? A.     The movement of a pair...
• 14M.2.sl.TZ1.7d: (i)     Identify the reagent necessary for this reaction to occur.   (ii)     Deduce the...
• 14M.2.sl.TZ2.6d: (i)     State the reagent required.   (ii)     Explain the mechanism of this reaction, using...
• 14N.2.hl.TZ0.10d: Transition metals and their compounds often catalyse reactions. The catalyzed decomposition of...
• 14N.1.sl.TZ0.29: Chloroethane, \({{\text{C}}_{\text{2}}}{{\text{H}}_{\text{5}}}{\text{Cl}}\), reacts with aqueous...
• 14N.2.sl.TZ0.7d: Explain the mechanism for the substitution reaction of bromoethane with sodium hydroxide. Use...
• 14N.3.sl.TZ0.26d: Propanone could also be formed from propene by reaction with steam over an acidic catalyst,...
• 13N.1.hl.TZ0.38: What is the major organic product formed from the reaction of (CH\(_3\))\(_3\)CBr with a...
• 13N.2.hl.TZ0.8e.i: Explain the mechanism of this reaction using curly arrows to represent the movement of electron...
• 13N.2.hl.TZ0.8e.iii: Suggest why, for some other halogenoalkanes, this hydrolysis is much more effective in alkaline...
• 13N.2.hl.TZ0.8g.i: Draw the structure of Y.
• 13N.2.hl.TZ0.8g.ii: State the reagent and any catalyst required for both the formation of Y and the conversion of Y...
• 13M.1.hl.TZ1.37: Which factors affect the rate of nucleophilic substitution in halogenoalkanes? I.     The nature...
• 13M.2.hl.TZ1.9d.ii: Halogenalkanes can react with NaOH via \({{\text{S}}_{\text{N}}}{\text{1}}\) and...
• 13M.2.hl.TZ1.9d.iii: Identify the rate-determining step of this mechanism.
• 13M.2.sl.TZ1.8d: Explain the mechanism for the reaction in (c) of...
• 13M.1.hl.TZ2.37: Which halogenoalkane reacts the fastest with hydroxide ions in a nucleophilic substitution...
• 12N.2.sl.TZ0.6a.vi: Explain one suitable mechanism for the reaction in (v) using curly arrows to represent the...
• 10N.3.hl.TZ0.G1d: Identify the organic product in the following...
• 10N.2.sl.TZ0.5e: (i)     State the meaning of each of the symbols in SN2. (ii)     Explain the mechanism of this...
• 10N.3.sl.TZ0.G2a: ...
• 09N.1.hl.TZ0.34: Which reaction occurs via a free-radical mechanism? A.    ...
• 09N.2.hl.TZ0.9c.i: State whether this reaction is SN1 or SN2.
• 09N.2.hl.TZ0.9c.ii: Explain the mechanism of the reaction using curly arrows to represent the movement of electron...
• 10M.2.hl.TZ1.7b.i: Identify the isomer(s) which will react with aqueous sodium hydroxide almost exclusively by an...
• 10M.2.hl.TZ1.7b.ii: Using the formula RBr to represent a bromoalkane, state an equation for the rate determining step...
• 10M.2.hl.TZ1.7b.iii: Identify one isomer that will react with aqueous sodium hydroxide almost exclusively by an...
• 10M.2.hl.TZ1.7c: State and explain how the rates of the reactions in parts (b) (i) and (b) (iii) are affected when...
• 10M.2.hl.TZ1.7d: State and explain how the rate of reaction of 1-bromobutane with sodium hydroxide compares with...
• 10M.3.hl.TZ1.G3b: Methylbenzene reacts when heated with a mixture of concentrated sulfuric acid and concentrated...
• 10M.2.sl.TZ1.6d: (i)     Isomer a is formed by reacting 1-bromobutane with aqueous sodium hydroxide. State...
• 10M.3.sl.TZ1.G2c: When but-1-ene reacts with hydrogen bromide, two possible organic products could be formed but in...
• 10M.3.sl.TZ2.G1b: Describe, using equations and curly arrows to represent the movement of electron pairs, the...
• 09M.1.hl.TZ1.37: Which statements about substitution reactions are correct? I.     The reaction between sodium...
• 09M.2.hl.TZ1.9a.ii: Identify the type of reaction and explain the mechanism for the preparation of but-1-ene from...
• 09M.2.hl.TZ1.9a.iii: State the equation (using structural formulas) for the preparation of 1-aminobutane from...
• 09M.2.hl.TZ1.9a.iv: Explain the mechanism for the preparation of 1-aminobutane from 1-bromobutane using curly arrows...
• 09M.2.hl.TZ1.9b.iii: Explain why the mechanism of the reaction will be different if 1-bromobutane is replaced by...
• 09M.2.hl.TZ2.8c: The reagents used in an elimination reaction are shown below. Explain the mechanism of this...
• 11M.2.hl.TZ1.7d.i: 2-chloro-3-methylbutane reacts with sodium hydroxide via an \({{\text{S}}_{\text{N}}}{\text{2}}\)...
• 11M.2.hl.TZ1.7d.ii: Explain why the hydroxide ion is a better nucleophile than water.
• 11M.1.sl.TZ1.27: What is the type of mechanism and an important feature of the reaction between...
• 11M.1.hl.TZ2.36: Halogenoalkanes can undergo \({{\text{S}}_{\text{N}}}{\text{1}}\) and...
• 11M.1.hl.TZ2.37: Propanitrile can be prepared by reacting bromoethane with potassium cyanide. Which statement is...
• 11M.2.hl.TZ2.8b.i: The reaction with 1-bromopentane proceeds by an \({{\text{S}}_{\text{N}}}{\text{2}}\) mechanism....
• 11M.2.hl.TZ2.8b.ii: The reaction with 2-bromo-2-methylbutane proceeds by an \({{\text{S}}_{\text{N}}}{\text{1}}\)...
• 11M.2.hl.TZ2.8b.iii: Explain why 1-bromopentane reacts by an \({{\text{S}}_{\text{N}}}{\text{2}}\) mechanism whereas...
• 11M.1.sl.TZ2.29: Which type of reaction occurs when 2-iodo-2-methylpropane,...
• 11N.1.hl.TZ0.37: Which halogenoalkane reacts fastest with sodium hydroxide? A.     1-iodobutane B.   ...
• 16M.1.hl.TZ0.35: ...
• 16M.1.hl.TZ0.36: ...
• 16M.2.hl.TZ0.2b: One important industrial use of phosgene is the production of polyurethanes. Phosgene is reacted...
• 16N.2.hl.TZ0.5d: Construct the mechanism of the formation of 2-bromopropane from hydrogen bromide and propene...
• 16N.2.hl.TZ0.6c: Suggest why the rate of alkaline hydrolysis of an enantiomer of iodopropane is greater than that...
• 17M.1.hl.TZ1.36: What is the product of the reduction of 2-methylbutanal? A.     2-methylbutan-1-ol B.    ...
• 17M.2.hl.TZ1.6c.iii: When the product X is reacted with NaOH in a hot alcoholic solution, C2H3Cl is formed. State the...
• 17M.2.hl.TZ1.7c: State the reagents used to convert benzene to nitrobenzene and the formula of the electrophile...
• 17M.2.hl.TZ1.7d: Explain the mechanism for the nitration of benzene, using curly arrows to show the movement of...
• 17M.2.hl.TZ1.7e: State the reagents used in the two-stage conversion of nitrobenzene to aniline.
• 17M.1.hl.TZ2.37: In which order should the reagents be used to convert benzene into phenylamine (aniline)?
• 17M.2.hl.TZ2.7c.i: State the reagents and the name of the mechanism for the nitration of benzene.
• 17M.2.hl.TZ2.7d: Below are two isomers, A and B, with the molecular formula C4H9Br. Explain the mechanism of...
• 17N.1.hl.TZ0.33: Propene reacts separately with H2O/H+ and H2/Ni to give products X and Z respectively.  What...
• 17N.1.hl.TZ0.35: What is the product of the reaction between pentan-2-one and sodium borohydride, NaBH4? A....
• 17N.2.hl.TZ0.8c: State the reagents used in the nitration of benzene.
• 17N.2.hl.TZ0.8d: State an equation for the formation of NO2+.
• 17N.2.hl.TZ0.8e: Explain the mechanism of the reaction between 2-bromo-2-methylpropane, (CH3)3CBr, and aqueous...
• 18M.1.hl.TZ1.37: Which reagents are needed to convert nitrobenzene to phenylamine in 2 steps?
• 18M.2.hl.TZ1.7a: Compare and contrast the mechanisms by which 1-chlorobutane, CH3CH2CH2CH2Cl, and...
• 18M.2.hl.TZ1.7b: Outline why the rate of reaction of the similar bromo-compounds is faster.
• 18M.2.hl.TZ1.7c.ii: Suggest how this product could be synthesized in one step from butanoic acid.
• 18M.1.hl.TZ2.35: Which is the correct combination of substitution reaction mechanisms?
• 18M.1.hl.TZ2.36: Propene is reacted first with hydrogen chloride to produce X which is then reacted with aqueous...
• 18M.2.hl.TZ2.9b.i: State the type of bond fission that takes place in a SN1 reaction.
• 18M.2.hl.TZ2.9b.ii: State the type of solvent most suitable for the reaction.
• 18M.2.hl.TZ2.9b.iii: Draw the structure of the intermediate formed stating its shape.
• 18M.2.hl.TZ2.9c: Nitrobenzene, C6H5NO2, can be converted to phenylamine via a two-stage reaction. In the first...

20.2 Synthetic routes

• 13N.2.hl.TZ0.2a: Deduce the structural formula of compound X.
• 13N.2.hl.TZ0.2b: State the reagents and conditions required for stage II of the...
• 13M.1.hl.TZ2.36: 1-bromobutane,...
• 10N.3.sl.TZ0.G3a: Deduce a two-step reaction pathway which can be used to convert 1-bromopropane into butanoic...
• 10N.3.sl.TZ0.G3b: Deduce a two-step reaction pathway which can be used to convert propan-2-ol into...
• 09N.2.hl.TZ0.9c.iii: The organic product obtained in part (c) (ii) can be reduced to form an amine. State an equation...
• 09N.1.sl.TZ0.29: Propene is converted to propanone in a two stage...
• 10M.2.sl.TZ1.3b.i: Chloroethene can be converted to ethanol in two steps. For each step deduce an overall equation...
• 09M.2.hl.TZ2.8b.ii: Propene to propanone.
• 11M.2.hl.TZ1.7a: Two compounds, A and D, each have the formula...
• 11M.2.hl.TZ1.7d.iii: 1-chlorobutane can be converted to a pentylamine via a two stage process. Deduce equations for...
• 11N.2.hl.TZ0.9b.iii: State the reagents and reaction conditions used to convert D to E and D to F directly.
• 16N.1.hl.TZ0.36: Which is correct for the conversion of propanal to propyl methanoate?
• 17M.2.hl.TZ1.7e: State the reagents used in the two-stage conversion of nitrobenzene to aniline.
• 17M.1.hl.TZ2.37: In which order should the reagents be used to convert benzene into phenylamine (aniline)?
• 18M.1.hl.TZ2.36: Propene is reacted first with hydrogen chloride to produce X which is then reacted with aqueous...

20.3 Stereoisomerism

• 15M.1.hl.TZ1.38: Which pair are geometric isomers?
• 15M.1.hl.TZ2.39: How many four-membered ring isomers are there of dichlorocyclobutane,...
• 15M.2.hl.TZ1.7d.i: 2-bromobutane exists as optical isomers. State the essential feature of optical isomers.
• 15M.2.hl.TZ1.7d.ii: 2-bromobutane exists as optical isomers. Outline how a polarimeter can distinguish between these...
• 15M.2.hl.TZ2.10h.i: Define the term stereoisomers.
• 15M.2.hl.TZ2.10h.ii: State the conditions needed for a compound to show cis-trans.
• 15M.2.hl.TZ2.10h.iii: Draw the structures of the two geometrical isomers of but-2-ene, clearly identifying each as cis...
• 14M.1.hl.TZ1.39: Which statement about isomerism is correct? A.     But-1-ene and but-2-ene are geometrical...
• 14M.1.hl.TZ2.37: What does a polarimeter measure? A.     Colour of reaction mixture B.     Polarity of a...
• 14M.1.hl.TZ2.38: Which compound can exist as stereoisomers? A.     1,2-dichloroethane B.   ...
• 14M.2.hl.TZ1.8e: (i)     Outline the meaning of the term stereoisomers.       (ii)     Draw the structures of...
• 14N.1.hl.TZ0.39: Which type(s) of stereoisomerism, if any, is/are present in the molecule CH2=CHCHBrCH3? A.    ...
• 13N.2.hl.TZ0.8c.i: State what is meant by optical activity.
• 13N.2.hl.TZ0.8c.ii: State what optical activity indicates about the structure of the molecule.
• 13N.2.hl.TZ0.8c.iii: Optical activity can be detected using a polarimeter. Explain how this works.
• 13N.2.hl.TZ0.8c.iv: Deduce the structural formula of X.
• 13M.1.hl.TZ1.34: What is the name of the following compound applying IUPAC rules? A.    ...
• 13M.1.hl.TZ1.38: Which molecule exhibits optical isomerism? A.     3-chloropentane B.     2-chlorobutane C.   ...
• 13M.2.hl.TZ1.9a.iv: State what is meant by the term stereoisomers.
• 13M.2.hl.TZ1.9a.v: Explain the existence of geometrical isomerism in but-2-ene.
• 13M.1.hl.TZ2.39: Which structure is a geometric isomer of cis-1,2-dichlorocyclobutane?
• 13M.2.hl.TZ2.8a: Describe what is meant by the term stereoisomers.
• 13M.2.hl.TZ2.8e.iii: State the instrument used to distinguish between each of the two enantiomers, and how they could...
• 13M.2.hl.TZ2.8e.iv: Compare the physical and chemical properties of enantiomers.   Physical...
• 12N.2.hl.TZ0.7a.i: State what is meant by the term stereoisomers.
• 12N.2.hl.TZ0.7c.iii: 2-bromobutane is optically active. Draw the two enantiomers of 2-bromobutane and compare their...
• 10N.1.hl.TZ0.39: Which statement about stereoisomers is correct? A. 1,2-dichloroethane has two geometrical...
• 10N.2.hl.TZ0.2b: But-2-ene shows geometrical isomerism. Draw the structural formula and state the name of the...
• 10N.2.hl.TZ0.5f: There are four structural isomers with the molecular formula...
• 10N.3.hl.TZ0.F5a: State its name and, by means of a diagram, predict its structure.
• 10N.3.hl.TZ0.F5b: Describe the structural feature of the carvone molecule that allows it to exist as optical isomers.
• 09N.1.hl.TZ0.37: Which compound could rotate the plane of polarization of polarized light? A.    ...
• 09N.2.hl.TZ0.9a.i: Draw the structural formulas of the two geometrical isomers of 1-chloro-but-2-ene.
• 09N.2.hl.TZ0.9a.ii: Explain why 1-chloro-but-2-ene shows geometrical isomerism.
• 09N.2.hl.TZ0.9a.iii: Draw the structural formula of one isomer of...
• 09N.3.hl.TZ0.F3a: Identify the chiral centre in this enantiomer with an asterisk, *.
• 09N.3.hl.TZ0.F3b: The \(( + )d\)-enantiomer has the characteristic smell of oranges and the \(( - )l\)-enantiomer...
• 09N.3.hl.TZ0.F3c: The R, S notation is also used. The \(( + )d\)-enantiomer is often described as R-limonene and...
• 10M.2.hl.TZ1.7e: Identify the isomer of C4H9Br that can exist as stereoisomers. Outline how a polarimeter will...
• 10M.2.hl.TZ2.5: (a)     Describe what is meant by the term stereoisomers. (b)     1,3-dichlorocyclobutane exists...
• 09M.1.hl.TZ1.39: Which compound can exist as stereoisomers? A.    ...
• 09M.2.hl.TZ1.9b.i: Draw the structures of the two mirror images of the isomer that can exhibit optical isomerism.
• 09M.2.hl.TZ1.9b.ii: Describe how the two optical isomers can be distinguished practically using plane-polarized light.
• 09M.1.hl.TZ2.39: Which statement is correct about the enantiomers of a chiral compound? A.     Their physical...
• 09M.2.hl.TZ2.8d.i: Describe geometrical isomerism.
• 09M.2.hl.TZ2.8d.ii: Draw the geometrical isomers of but-2-ene.
• 09M.2.hl.TZ2.8d.iii: Draw the two enantiomers of butan-2-ol.
• 11M.1.hl.TZ1.33: Which molecule has a chiral centre? A.    ...
• 11M.1.hl.TZ1.35: Which two molecules are cis-trans isomers of each other? A.     X and Z B.     X and Y C.   ...
• 11M.1.hl.TZ2.39: Which compound is optically active?
• 11M.2.hl.TZ2.8a: Deduce the name of one of the isomers which can exist as enantiomers and draw three-dimensional...
• 12M.3.hl.TZ1.D3b: The action of a drug molecule often depends on its shape. Discuss a specific example of a drug...
• 12M.1.hl.TZ2.38: Which compound has a chiral carbon? A.     Propan-2-ol B.     1-bromo-2-methylbutane C.   ...
• 12M.1.hl.TZ2.39: What effect of optical isomers on plane-polarized light can be measured using a polarimeter? A. ...
• 11N.1.hl.TZ0.38: Which molecule exhibits optical isomerism? A.     3-iodopentane B.   ...
• 11N.3.hl.TZ0.D4a: Using an asterisk (*), identify the chiral carbon atom in the structure of thalidomide.
• 11N.3.hl.TZ0.D4b: Describe the composition of a racemic mixture.
• 11N.1.sl.TZ0.28: From which monomer is this polymer made?
• 16M.1.hl.TZ0.37: ...
• 16M.3.hl.TZ0.10c: (i) Serine is a chiral amino acid. Draw both enantiomers of serine. (ii) State the enantiomeric...
• 16M.3.hl.TZ0.26c: Oseltamivir is a chiral compound. (i) Identify an apparatus that can be used to distinguish...
• 16N.1.hl.TZ0.37: Which statement is correct for a pair of enantiomers under the same conditions? A.  A racemic...
• 16N.2.hl.TZ0.6a: Draw the three-dimensional shape of each enantiomer of this isomer showing their spatial...
• 16N.2.hl.TZ0.6b: When one enantiomer undergoes substitution by alkaline hydrolysis approximately 75 % of the...
• 17M.1.hl.TZ1.37: Which molecule is chiral? A.     2-chlorobutane B.     2,2-dichloropentane C.    ...
• 17M.3.hl.TZ1.17: Vision is dependent on retinol (vitamin A) present in retina cells. Retinol is oxidized to...
• 17M.3.hl.TZ1.28a: Describe what happens to plane-polarized light when it passes through a solution of an optically...
• 17M.3.hl.TZ1.28b: A mixture of enantiomers shows optical rotation. Suggest a conclusion you can draw from this data.
• 17M.1.hl.TZ2.35: Which pair of isomers always shows optical activity? A.     Cis-trans B.     Enantiomers C.  ...
• 17M.2.hl.TZ2.7d: Below are two isomers, A and B, with the molecular formula C4H9Br. Explain the mechanism of...
• 17N.1.hl.TZ0.37: What is the number of optical isomers of isoleucine? A. 0 B. 2 C. 4 D. 8
• 17N.2.hl.TZ0.8a.iv: Deduce, giving a reason, which of the two compounds can show optical activity.
• 17N.2.hl.TZ0.8a.v: Draw three-dimensional representations of the two enantiomers.
• 18M.1.hl.TZ1.35: What is name of this compound applying IUPAC rules? A.     E 1-bromo-1-chlorobut-1-ene B.   ...
• 18M.1.hl.TZ1.36: Which molecule contains a chiral carbon? A.     CH3CH2CHBrCH2CH3 B.     CH3CH2CHBrCH3 C.   ...
• 18M.1.hl.TZ2.37: Which isomers exist as non-superimposable mirror images? A.     cis-trans isomers B.   ...
• 18M.2.hl.TZ2.9b.iv: Suggest, giving a reason, the percentage of each isomer from the SN1 reaction.
• 18M.3.hl.TZ2.8e: Sketch the wedge and dash (3-D) representations of alanine enantiomers.