DP Chemistry Questionbank

State the name of Compound B, applying International Union of Pure and Applied Chemistry (IUPAC) rules.

The structures of two molecules, X and Y, are shown below.

(i) Justify why both these molecules are carbohydrates.

(ii) Distinguish between these molecules in terms of their functional groups.

Identify the functional groups which are present in only one structure of glucose.

Chloroethene, C₂H₃Cl, can undergo polymerization. Draw a section of the polymer with three repeating units.

The overall equation for monochlorination of methane is:

CH₄(g) + Cl₂(g) → CH₃Cl(g) + HCl(g)

Calculate the standard enthalpy change for the reaction, ΔH ^θ, using section 12 of the data booklet.

Draw the structure of the dipeptide Asp–Phe using section 33 of the data booklet.

Deduce the structural formulas of the two possible isomers.

Explain why the difference in their structures affects their melting points.

Deduce the name of the class of compound formed when the product of (c)(i) reacts with butanoic acid.

The compound could not be oxidized using acidifi ed potassium dichromate(VI).

Deduce the structural formula of the compound.

Draw the structural formula of propan-2-ol.

Draw two structural isomers of methyloxirane.

Which alcohols are oxidized by acidified potassium dichromate(VI) solution when heated?

A. I and II only 

B. I and III only 

C. II and III only 

D. I, II and III

Explain why the compound C₂H₆O, produced in (b), has a higher boiling point than compound C₂H₄O, produced in d(i).

In which order should the reagents be used to convert benzene into phenylamine (aniline)?

Outline one piece of physical evidence for the structure of the benzene ring.

Draw the structure of one other isomer of xylene which retains the benzene ring.

State the name of the functional group which allows the molecule to be responsive to applied electric fields.

Compare and contrast the functional groups present in methadone and diamorphine (heroin), giving their names. Use section 37 of the data booklet.

Which compound has the lowest boiling point?

A. CH₃CH₂CH₂CH₂CH₂CH₃

B. CH₃CH₂CH₂CH₂CH₃

C. CH₃CH(CH₃)CH₂CH₃

D. CH₃C(CH₃)₂CH₃

Which compound has the lowest boiling point?

A. CH₃CH₂CH₂CH₂CH₂CH₃

B. CH₃CH₂CH₂CH₂CH₃

C. CH₃CH(CH₃)CH₂CH₃

D. CH₃C(CH₃)₂CH₃

Deduce the formula of the biodiesel formed when the vegetable oil shown is reacted with the reagents in (a).

State the reagents and the name of the mechanism for the nitration of benzene.

Which compound contains a secondary carbon atom?

A.     CH₃CH(Cl)CH(CH₃)₂

B.     (CH₃)₂CHCH₂Cl

C.     (CH₃)₃CCl

D.     CH₃CH₂Cl

Which molecule has a tertiary nitrogen?

A.     (CH₃)₂NH

B.     (C₂H₅)₄N⁺I⁻

C.     C₃H₇N(CH₃)₂

D.     C₆H₅NH₂

Suggest the structural formula of this compound.

State the reagents used to convert benzene to nitrobenzene and the formula of the electrophile formed.

Draw the structure of the dipeptide Asp–Phe using section 33 of the data booklet.

Explain why the ¹H NMR spectrum of C₃H₆O, produced in (d)(i), shows only one signal.

Hydrogenation of propene produces propane. Calculate the standard entropy change, ΔS^θ, for the hydrogenation of propene.

Infrared (IR) spectroscopy is used to identify functional groups in organic compounds.

Deduce the wavenumber, in cm⁻¹, of an absorption peak found in the IR spectrum of testosterone but not in that of cholesterol.

Subsequent steps proceed under differing conditions, forming the dendrimer polymer with the following repeating unit.

State the name of one functional group in this repeating unit.

Explain why the compound C₃H₈O, produced in (a)(iv), has a higher boiling point than compound C₃H₆O, produced in d(i).

State the typical reactions that benzene and cyclohexene undergo with bromine.

What are the functional groups in the aspirin molecule?

A.     I and II only

B.     I and III only

C.     II and III only

D.     I, II and III

Discuss the physical evidence for the structure of benzene.

Bromine was added to hexane, hex-1-ene and benzene. Identify the compound(s) which will react with bromine in a well-lit laboratory.

What is the order of increasing boiling point for the isomers of C₅H₁₂?

A.   CH₃CH₂CH₂CH₂CH₃ < CH₃CH(CH₃)CH₂CH₃ < CH₃C(CH₃)₃

B.   CH₃C(CH₃)₃ < CH₃CH(CH₃)CH₂CH₃ < CH₃CH₂CH₂CH₂CH₃

C.   CH₃C(CH₃)₃ < CH₃CH₂CH₂CH₂CH₃ < CH₃CH(CH₃)CH₂CH₃

D.   CH₃CH(CH₃)CH₂CH₃ < CH₃C(CH₃)₃ < CH₃CH₂CH₂CH₂CH₃

State the name of product B, applying IUPAC rules.

One possible Lewis structure for benzene is shown.

State one piece of physical evidence that this structure is incorrect.

Ethane, C₂H₆, reacts with chlorine in sunlight. State the type of this reaction and the name of the mechanism by which it occurs.

Which compound with the molecular formula ${\mathrm{C}}_4{\mathrm{H}}_8\mathrm{O}$ has this high resolution ${}_1\mathrm{H} \mathrm{NMR}$?

From: libretexts.org. Courtesy of Chris Schaller, Professor (Chemistry)
at College of Saint Benedict/Saint John’s University.

A.  but-3-en-2-ol, ${\mathrm{CH}}_2=\mathrm{CHCH}\left(\mathrm{OH}\right){\mathrm{CH}}_3$

B.  butanal, ${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2\mathrm{CHO}$

C.  butanone, ${\mathrm{CH}}_3{\mathrm{COCH}}_2{\mathrm{CH}}_3$

D.  but-3-en-1-ol, ${\mathrm{CH}}_2={\mathrm{CHCH}}_2{\mathrm{CH}}_2\mathrm{OH}$

Bromine was added to hexane, hex-1-ene and benzene. Identify the compound(s) which will react with bromine in a well-lit laboratory.

Describe the difference in their structures.

Describe two differences, other than the number of atoms, between the models of ethane and ethene constructed from the kit shown.

Compound A and B are isomers. Draw two other structural isomers with the formula ${\mathrm{C}}_3{\mathrm{H}}_6\mathrm{O}$.

The above ball and stick model is a substituted pyridine molecule (made of carbon, hydrogen, nitrogen, bromine and chlorine atoms). All atoms are shown and represented according to their relative atomic size.

Label each ball in the diagram, excluding hydrogens, as a carbon, C, nitrogen, N, bromine, Br, or chlorine, Cl.

Identify one organic functional group that can react with acidified K₂Cr₂O₇(aq).

Identify the functional group that shows stretching at 1710 cm^–1 in the infrared spectrum of this compound using section 26 of the data booklet and the ¹H NMR.

One possible product, X, of the reaction of ethane with chlorine has the following composition by mass:

carbon: 24.27%, hydrogen: 4.08%, chlorine: 71.65%

Determine the empirical formula of the product.

Describe a technique for the detection of steroids in blood and urine.

State the name of Compound A, applying International Union of Pure and Applied Chemistry (IUPAC) rules.

Suggest two absorbances, other than the absorbances due to the ring structure and C–H bonds, that would be present in the infrared (IR) spectrum of aspirin.

One possible product, X, of the reaction of ethane with chlorine has the following composition by mass:

carbon: 24.27%, hydrogen: 4.08%, chlorine: 71.65%

Determine the empirical formula of the product.

Ethoxyethane (diethyl ether) can be used as a solvent for this conversion. Draw the structural formula of ethoxyethane

Explain how redox chemistry is used to measure the ethanol concentration in a breathalyser.

Pyridine, like benzene, is an aromatic compound.

Outline what is meant by an aromatic compound.

Suggest a wavenumber absorbed by methane gas.

Which spectra would show the difference between propan-2-ol, CH₃CH(OH)CH₃, and propanal, CH₃CH₂CHO?

I.   mass
II.  infrared
III. ¹H NMR

A.  I and II only

B.  I and III only

C.  II and III only

D.  I, II and III

The Kekulé structure of benzene suggests it should readily undergo addition reactions.

Discuss two pieces of evidence, one physical and one chemical, which suggest this is not the structure of benzene.

Write the equation and name the organic product when ethanol reacts with methanoic acid.

Compound A and B are isomers. Draw two other structural isomers with the formula ${\mathrm{C}}_3{\mathrm{H}}_6\mathrm{O}$.

Using relevant equations, show the initiation and the propagation steps for this reaction.

Ethoxyethane (diethyl ether) can be used as a solvent for this conversion.
Draw the structural formula of ethoxyethane

The IR spectrum of one of the compounds is shown:

COBLENTZ SOCIETY. Collection © 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved.

Deduce, giving a reason, the compound producing this spectrum.

Draw the structure of one other isomer of xylene which retains the benzene ring.

The IR spectrum of one of the compounds is shown:

COBLENTZ SOCIETY. Collection © 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved.

Deduce, giving a reason, the compound producing this spectrum.

Suggest a wavenumber absorbed by methane gas.

Suggest two differences in the ¹H NMR of but-2-ene and the organic product from (d)(ii).

Deduce the splitting pattern in the ¹H NMR spectrum for 1-bromopropane.

Determine the enthalpy change for the reaction, in kJ, to produce A using section 11 of the data booklet.

Suggest two differences in the ¹H NMR of but-2-ene and the organic product from (d)(ii).

The mass and ¹H NMR spectra of product X are shown below. Deduce, giving your reasons, its structural formula and hence the name of the compound.

One possible Lewis structure for benzene is shown.

State one piece of physical evidence that this structure is incorrect.

The mass and ¹H$$NMR spectra of product X are shown below. Deduce, giving your reasons, its structural formula and hence the name of the compound.

Which is a homologous series?

A.  C₂H₄, C₃H₅, C₄H₆

B.  C₂H₂, C₃H₄, C₄H₆

C.  C₂H₂, C₂H₄, C₂H₆

D.  C₂H₂, C₄H₄, C₆H₆