10.1 Fundamentals of organic chemistry

Deduce the structural formulas of the two possible isomers.

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

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

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

Deduce the structural formulas of the two possible isomers.

One possible Lewis structure for benzene is shown.

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

Deduce the structural formulas of the two possible isomers.

Draw the structural formula of propan-2-ol.

One possible Lewis structure for benzene is shown.

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

One possible Lewis structure for benzene is shown.

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

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.

One possible Lewis structure for benzene is shown.

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

One possible Lewis structure for benzene is shown.

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

One possible Lewis structure for benzene is shown.

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

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

Draw the structural formula of propan-2-ol.

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

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.

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.

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

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

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

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.

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.

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.

Draw the structural formula of propan-2-ol.

Pyridine, like benzene, is an aromatic compound.

Outline what is meant by an aromatic compound.

Pyridine, like benzene, is an aromatic compound.

Outline what is meant by an aromatic compound.

Pyridine, like benzene, is an aromatic compound.

Outline what is meant by an aromatic compound.

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

Deduce the structural formula of the compound.

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

Deduce the structural formula of the compound.

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

Deduce the structural formula of the compound.

Draw two structural isomers of methyloxirane.

Draw two structural isomers of methyloxirane.

Draw two structural isomers of methyloxirane.

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

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

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

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

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

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

State the name of product B, applying IUPAC rules.

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

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

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

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

State the name of product B, applying IUPAC rules.

State the name of product B, applying IUPAC rules.

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

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.

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

Which compound has the lowest boiling point?

A. CH₃CH₂CH₂CH₂CH₂CH₃

B. CH₃CH₂CH₂CH₂CH₃

C. CH₃CH(CH₃)CH₂CH₃

D. CH₃C(CH₃)₂CH₃

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

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

Which compound has the lowest boiling point?

A. CH₃CH₂CH₂CH₂CH₂CH₃

B. CH₃CH₂CH₂CH₂CH₃

C. CH₃CH(CH₃)CH₂CH₃

D. CH₃C(CH₃)₂CH₃

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

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

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

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.

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

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.

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

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

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.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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, ${\mathrm{CH}}_2={\mathrm{CHCH}}_2{\mathrm{CH}}_2\mathrm{OH}$

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, ${\mathrm{CH}}_2={\mathrm{CHCH}}_2{\mathrm{CH}}_2\mathrm{OH}$

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

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

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

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

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.

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.

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.

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.

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.

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.

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

Suggest a wavenumber absorbed by methane gas.

Suggest a wavenumber absorbed by methane gas.

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

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

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

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

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

Suggest a wavenumber absorbed by methane gas.

Suggest a wavenumber absorbed by methane gas.

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

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

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

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

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

Which is a homologous series?

A.  C₂H₄, C₃H₅, C₄H₆

B.  C₂H₂, C₃H₄, C₄H₆

C.  C₂H₂, C₂H₄, C₂H₆

D.  C₂H₂, C₄H₄, C₆H₆

Which is a homologous series?

A.  C₂H₄, C₃H₅, C₄H₆

B.  C₂H₂, C₃H₄, C₄H₆

C.  C₂H₂, C₂H₄, C₂H₆

D.  C₂H₂, C₄H₄, C₆H₆

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

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

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

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

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

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

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

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.

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

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

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

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

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

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

Which homologous series has the general formula C_nH_2nO (n > 2)?

A.  Alcohols

B.  Carboxylic acids

C.  Ethers

D.  Ketones

Which homologous series has the general formula C_nH_2nO (n > 2)?

A.  Alcohols

B.  Carboxylic acids

C.  Ethers

D.  Ketones

2-Bromobutane reacts with hydroxide via the same mechanism identified in (b). Explain this mechanism using curly arrows to represent the movement of electron pairs.

2-Bromobutane reacts with hydroxide via the same mechanism identified in (b). Explain this mechanism using curly arrows to represent the movement of electron pairs.

2-Bromobutane reacts with hydroxide via the same mechanism identified in (b). Explain this mechanism using curly arrows to represent the movement of electron pairs.