OCHEM final exam study set

Which of the following lists contains common heteroatoms found in organic molecules?

A) N, O, S, P, Cl

B) Na, O, S, P, Cl

C) Na, Mg, S, N, Cl

D) Na, Mg, O, N, Cl

A

Which of the following molecules contain the same functional groups?

A) I, II, IV

B) I, II, III

C) II, III, IV

D) I, III, IV

A

Which of the following correctly matches the molecules to the names of the functional groups?

C

Which of the following correctly matches the molecules to the names of the functional groups?

A) I and II

B) II and III

C) III and IV

D) I and III

D

Consider the molecule donepezil (used to treat Alzheimer's disease). Which of the following lists the correct functional groups present in donepezil?

A) Amide, aromatic, ether, ketone

B) Amide, aromatic , ester, ketone

C) Amine, aromatic, ester, ketone

D) Amine, aromatic, ether, ketone

D

Consider the molecule atenolol (a b blocker used to treat hypertension). Which of the following lists the correct functional groups present in atenolol?

A) Primary alcohol, amide, primary amine, aromatic, ether

B) Secondary alcohol, amide, secondary amine, aromatic, ether

C) Secondary alcohol, amide, primary amine, aromatic, ether

D) Secondary alcohol, amide, secondary amine, aromatic, ester

B

Which of the following structures contain an amide?

A) I

B) II

C) III

D) IV

D

Which of the following compounds has the lowest boiling point?

A) I

B) II

C) III

D) IV

D

Which of the following compounds has the highest boiling point?

A) I

B) II

C) III

D) IV

D) IV

Which of the following list the correct functional groups found in aspartame, the artificial sweetener?

A) Amine, aromatic, carboxylic acid, ether, ketone

B) Amine, amide, aromatic, carboxylic acid, ether

D) Amine, aromatic, carboxylic acid, ester, nitrile

B

Why do heteroatoms confer reactivity on a particular molecule?

A) Because they have lone pairs and create electron-rich sites on carbon

B) Because they have lone pairs and create electron-deficient sites on carbon

C) Because they are electronegative and act as electrophiles

B

Why do pi bonds confer reactivity on a particular molecule?

A) Because pi bonds are difficult to break in chemical reactions

B) Because pi bonds make a molecule an acid

C) Because pi bonds are easily broken in chemical reactions

D) Because pi bonds make a molecule an electrophile

C

Which of the following molecules contain the same functional groups?

A) I, II, III

B) I, II, IV

C) II, III, IV

D) I, III, IV

D

Which of the following molecules are aliphatic hydrocarbons?

A) I, II, and III

B) I and III

C) II, III, IV

D) II and IV

B

Which of the following molecules are aromatic hydrocarbons?

A) I

B) II

C) III

D) I and II

D

Which of the following correctly matches the molecules to the names of the functional group?

B

Which of the following structures contains a secondary amine?

A) I

B) II

C) III

D) IV

C

Which of the following structures contains a primary amine?

A) I

B) II

C) III

D) IV

A

Which of the following structures contains an alkene?

A) I

B) II

C) III

D) IV

B

Which of the following is a tertiary amine?

A) I

B) II

C) III

D) IV

B

Which of the following is a secondary alcohol?

A) I

B) II

C) III

D) IV

D

Which of the following statements best describes the relationship between the surface area of a molecule and the strength of the intermolecular forces?

A) The larger the surface area, the weaker the intermolecular force

B) The larger the surface area, the stronger the intermolecular forces

C) The smaller the surface area, the stronger the intermolecular forces

D) There is no relationship

B

Rank the following compounds in order of increasing strength of intermolecular forces, putting the molecule with the weakest intermolecular force first

A) I < II < III

B) II < I < III

C) I < III < II

D) II < III < I

C

Which of the following compounds has the highest boiling point?

A) I

B) II

C) III

D) IV

D

Which of the following compounds has the highest boiling point?

A) I

B) II

C) III

D) IV

B

Which of the following compounds has the highest boiling point?

A) I

B) II

C) III

D) IV

A

Rank the following compounds in order of decreasing boiling point, putting the compound with the highest boiling point first.

A) I > II > III > IV

B) III > IV > II > I

C) III > II > IV > I

D) I > IV > II > III

C

Which of the following compounds can form intermolecular hydrogen bonds with a molecule similar to itself?

A) I

B) II

C) III

D) IV

D

What is the strongest intermolecular force present in 1-propanol?

A) Ion-ion

B) hydrogen bonding

C) Dipole-dipole

D) Induced dipole-induced dipole

B

What intermolecular force is generally considered the strongest?

A) Hydrogen bonding

B) London dispersion forces

C) Covalent bonds

D) Dipole-dipole

A

What intermolecular force is generally considered the weakest?

A) Hydrogen bonding

B) London dispersion forces

C) Dipole-dipole

D) Ion-ion

B

Rank the following compounds in order of increasing melting point, putting the compound with the least melting point first.

A) II < I < III

B) I < III < II

C) I < II < III

D) III < II < I

C

Rank the following compounds in order of decreasing melting point, putting the compound with the highest melting point first.

A) I > II > III

B) II > III > I

C) III > II > I

D) III > I > II

D

Which of the following intermolecular forces would not form between similar molecules of the structure below?

A) London dispersion forces

B) Ion-ion

C) Hydrogen bonding

D) Dipole-dipole

B

Which of the following alkenes is expected to have the highest melting point?

A) I

B) II

C) III

D) IV

D

Which of the following compounds is expected to be the least soluble in H2O

A) I

B) II

C) III

D) IV

A

Which of the following compounds is expected to be the most soluble in H2O?

A) I

B) II

C) III

D) IV

B

Which of the following compounds would be expected to be more soluble in hexane (C6H14)?

A) I

B) II

C) III

D) IV

A

Which of the following statements about the solubility of organic compounds in H2O is true?

A) The non-polar part of a molecule that is not attracted to water is said to be hydrophilic

B) The non-polar part of a molecule that is not attracted to water is said to be hydrophobic

C) The polar part of a molecule that can hydrogen bond to water is said to be hydrophobic

D) For an organic compound with one functional group that contains an O or N atom the compound is water soluble only if it has ≥ 5 carbons

B

Which of the following compounds is expected to be H2O soluble?

A) I

B) II

C) III

D) IV

B

What molecular features are required for soap to properly dissolve grease and oil?

A) The molecule must be large

B) The molecule must contain a polar head

C) The molecule must contain a non-polar tail

D) B and C are required

D

Which of the following statements about vitamin A, are true?

A) Vitamin A is soluble in H2O

B) Vitamin A is insoluble in organic solvents

C) Vitamin A contains an aromatic ring

D) Vitamin A is insoluble in H2O

D

Which of the following statements about vitamin C are true?

A) Vitamin C is insoluble in H2O

B) Vitamin C is soluble in H2O

C) Vitamin C is an aliphatic hydrocarbon

D) Vitamin C contains a ketone functional group

B

Which of the following could most likely serve as an ionophore?

A) I

B) II

C) III

D) IV

D

The indicated carbon atom is:

A) Electrophilic because it is electron-deficient

B) Nucleophilic because it is electron-deficient

C) Electrophilic because it is electron-rich

D) Nucleophilic because it is electron-rich

A

The indicated bond is:

A) Nucleophilic because it is electron-deficient

B) Electrophilic because it is electron-deficient

C) Nucleophilic because it is electron-rich

D) Electrophilic because it is electron-rich

C

The indicated bond is:

A) Nucleophilic because it is electron-deficient

B) Electrophilic because it is electron-rich

C) Nucleophilic because it is electron-rich

D) Electrophilic because it is electron-deficient

D

Rank the following compounds in order of decreasing boiling point, putting the compound with the highest boiling point first

A) I > III > IV > II

B) IV > II > I > III

C) IV > I > II > III

D) I > IV > II > III

D

Which of the following compounds has only primary and secondary carbon atom?

A) Pentane

B) 2-Methylpentane

C) 2,2-Dimethylpentane

D) 2,3,3-Trimethylpentane

A

What is the parent chain for the following compound?

A) Hexane

B) Heptane

C) Octane

D) Nonane

B

What is the IUPAC name for the following compound?

A) 3-Ethyl-2,7-dimethyl-5-sec-butyldecane

B) 5-sec-Butyl-3-ethyl-2,7-dimethyldecane

C) 2,7-Dimethyl-3-ethyl-5-sec-butyldecane

D) 3-Ethyl-2,7-dimethyl-5-isobutyldecane

B

What is the IUPAC name for the following compound?

A) 3-ethyl-1-methylcyclohexane

B) 1-ethyl-3-methylcyclohexane

C) 1-ethyl-3-methylhexane

D) 3-ethyl-1-methylhexane

B

Rank the following alkanes in order of decreasing boiling point, putting the alkane with the highest boiling point first.

A) I > II > III

B) I > III > II

C) II > III > I

D) III > II > I

B

Rank the following alkanes in order of increasing melting point, putting the alkane with the lowest melting point first.

A) I < III < II

B) I < II < III

C) II < III < I

D) III < II < I

A

Which of the following are anti-conformers?

A) I and II

B) II and III

C) I and IV

D) II and IV

D

Which of the following conformers has the highest energy?

A) I

B) II

C) III

D) IV

B

Which of the following is the highest energy conformer of 2,3-dimethylbutane?

A) I

B) II

C) III

D) IV

C

Which of the following is the lowest energy conformer of 2,3-dimethylbutane?

A) I

B) II

C) III

D) IV

B

Which of the following is the most stable conformation of cis-1-ethyl-3-isopropylcyclohexane?

A) I

B) II

C) III

D) IV

C

Which of the following statements about alkanes is not true?

A) Alkanes are aliphatic hydrocarbons

B) Alkanes contain only C-C and C-H s bonds

C) Alkanes are acyclic or cyclic

D) Acyclic alkanes have two fewer H atoms than cyclic alkanes with the same number of carbons

D

Which of the following statements about alkanes is true?

A) Alkanes are aliphatic hydrocarbons having only C-C and C-H pi bonds

B) Cyclic alkanes have two fewer H atoms than acyclic alkanes contain carbons joined in one or more rings

C) Acyclic alkanes contain carbons joined in one or more rings

D) Acyclic alkanes have general molecular formula CnH2n

B

What is the molecular formula of an alkane that has twenty-three carbon atoms?

B

What is the molecular formula of a cycloalkane that has six carbon atoms?

C

What is the approximate C-C-C bond angle in propane?

A) 90

B) 109.5

C) 120

D) 180

B

What is the hybridization of a carbon atom in an alkane?

A) sp3

B) sp2

C) sp

D) p

A

How many constitutional isomers are there with the molecular formula C5H12

A) 2

B) 3

C) 4

D) 5

B

How many constitutional isomers are there with the molecular formula C6H14?

A) 2

B) 3

C) 4

D) 5

D

Which of the following is not another representation for 2-methylbutane?

D

Which of the following compounds has primary, secondary, tertiary, and quaternary carbon atoms?

A) Pentane

B) 2-methylpentane

C) 2,2-dimethylpentane

D) 2,2,3-trimethylpentane

D

Which of the following compounds has only primary, secondary, and tertiary carbon atoms?

A) Pentane

B) 2-methylpentane

C) 2,2-dimethylpentane

D) 2,2,3-trimethylpentane

B

Which of the following compounds has only primary, secondary, and quaternary carbon atoms?

A) Pentane

B)2-methylpentane

C) 2,2-dimethylpentane

D) 2,2,3-trimethylpentane

C

Which of the following compounds has primary, secondary, and tertiary hydrogen atoms

A) Pentane

B) Hexane

C) 2-methylpentane

D) 2,2-dimethylpentane

C

Which of the following compounds has only primary and secondary hydrogen atoms?

A) 2-methylpentane

B) 2,2,3-trimethylpentane

C) 3-methylpentane

D) 2,2-dimethylpentane

D

How many cycloalkane constitutional isomers (excluding stereoisomers) are there with molecular formula C5H10

A) 2

B) 3

C) 4

D) 5

D

What is the parent chain for the following compound?

A) Heptane

B) Octane

C) Nonane

D) Decane

C

What is the name of the alkyl group that contains two carbons in a straight chain and one-carbon branch?

A) ethyl

B) Propyl

C) isopropyl

D) None

C

What is the IUPAC name for the following compound?

A) 4-ethyl-5-methyloctane

B) 4-methyl-5-ethyloctane

C) 4-methyl-3-propylheptane

D) 4-methyl-5-propyloctane

A

What is the IUPAC name for the following compound?

A) 3,5-diethyl-6-methylheptane

B) 3,5-diethyl-2-methylheptane

C) 3-ethyl-5-isopropylheptane

D) 5-ethyl-3-isopropylheptane

B

What is the IUPAC name for the following compound?

A) 2,3-dimethyl-4-sec-butylheptane

B) 4-sec-butyl-2,3-dimethylheptane

C) 3,5,6-trimethyl-4-propylheptane

D) 2,3,5-trimethyl-4-propylheptane

D

What is the IUPAC name for the following compound?

A) 5-ethyl-3,6-dimethylheptane

B) 3-ethyl-2,5-dimethylheptane

C) 3-ethyl-2,5-dimethyloctane

D) 5-ethyl-3,6-dimethyloctane

B

What is the IUPAC name for the following compound?

A) 2,3,5-trimethylhexane

B) 2,4,5-triethylhexane

C) 2,4-diethyl-5-methylheptane

D) 4-ethyl-3,6-dimethyloctane

D

What is the IUPAC name for the following compound?

A) 1-sec-butyl-4-isopropyl-2-methylcyclohexane

B) 1-isopropyl-3-methyl-4-sec-butylcyclohexane

C) 4-isopropyl-2-methyl-1-sec-butylcyclohexane

D) 1-sec-butyl-3-isopropyl-2-methylcyclohexane

A

What is the IUPAC name for the following compound?

A) 1,4-dimethylcyclohexane

B) 1,3-dimethylcyclohexane

C) 1,3-dimethylcyclopentane

D) 1,4-dimethylcyclopentane

C

What is the IUPAC name for the following compound?

A) 1-butylcyclohexane

B) Cyclohexanebutane

C) 1-CYclohexylbutane

D) Butylcyclohexane

D

What is the IUPAC name for the following compound?

A) Hexylcyclopentane

B) 1-Hexylcyclopentane

C) 1-cyclopentlyhexane

D) 1-cyclopentylheptane

C

What is the IUPAC name for the following compound?

A) 1-butyl-3-methylcyclohexane

B) 1-sec-butyl-3-methylcyclohexane

C) 1-methyl-3-sec-butylcyclohexane

D) 1-sec-butyl-3-methylhexane

B

What is the common name of the following alkyl group?

A) isobutyl

B) sec-butyl

C) isopropyl

D) tert-butyl

B

What is the common name of the following alkyl group?

A) Isopropy

B) Isobutyl

C) sec-butyl

D) Tert-butyl

A

Which of the following statements about the conformations of acyclic alkanes is true?

A) Conformations are the same arrangements of atoms that cannot be interconverted

B) In the eclipsed conformation, the C-H bonds on one carbon bisect the H-C-H bond angle on the adjacent carbon

C) In the staggered conformation, the C-H bonds on one carbon are directly aligned with the C-H bonds on the adjacent carbon

D) Rotating the atoms on one carbon by 6p converts an eclipsed conformation into a staggered conformation, and vice versa

D

Which of the following statements about the conformations of acyclic alkanes is not true?

A) The staggered and eclipsed conformations are equally stable

B) The staggered conformations are more stable than the eclipsed conformations

C) An energy minimum and maximum occur every 60 as the conformation changes from staggered to eclipsed

D) Conformations that are neither staggered nor eclipsed are intermediate in energy

A

Which of the following statements about the conformations of acyclic alkanes is true/

A) A staggered conformation with two larger groups 180 from each other is called gauche

B) staggered conformations are at energy maxima and eclipsed conformations are energy minima

C) A staggered conformation with two larger groups 60 form each other is called anti

D) Gauche conformers are generally higher in energy than anti conformations

D

Which of the following is not a conformer of butane?

A) I

B) II

C) III

D) IV

D

Which of the following are gauche conformers?

A) I and II

B) I and III

C) II and IV

D) II and III

B

Rank the conformers of butane in order of decreasing stability, putting the most stable first

A) IV > I > II > III

B) IV > I > III > II

C) II > III > I > IV

D) I > IV > II > III

B

Which of the following cycloalkanes has the most angle strain?

A) cyclopropane

B) cyclobutane

C) cyclopentane

D) cyclohexane

A

Which of the following cycloalkanes has the least angle strain/

A) cyclopropane

B) Cyclohexane

C) cyclopentane

D) cycloheptane

B

Which of the following chair conformations represents trans-1,3-dimethylcyclohexane?

A) I

B) II

C) III

D) IV

D

Which of the following chair conformations represents trans-1,4-dimethylcyclohexane?

A) I

B) II

C) III

D) IV

A

Which of the following is the most stable conformation of trans-1-isopropyl-3-methylcyclohexane?

A) I

B) II

C) III

D) IV

D

Select the most stable conformer of cis-1,3-cyclohexanediol

A) I

B) II

C) III

D) IV

B