Question 1

Which of the following statements best describes a structural (constitutional) isomer in organic chemistry?

Accepted Answer

Molecules with the same molecular formula but different connectivity of atoms.

Question 2

Which of the following compounds is aromatic according to Hückel's rule?

Accepted Answer

Benzene

Question 3

A student reacts 2-bromopropane with sodium ethoxide in ethanol. Which type of reaction mechanism is most likely to occur?

Accepted Answer

E2 elimination

Question 4

Which of the following is the correct IUPAC name for the compound $$CH_3CH_2CH_2CH_2CH_3$$?

Accepted Answer

Pentane

Question 5

Which of the following statements about cyclohexane conformations is correct?

Accepted Answer

The chair conformation is more stable than the boat conformation.

Question 6

Which of the following molecules is a meso compound?

Accepted Answer

2,3-dibromobutane (with opposite stereochemistry at each carbon)

Question 7

What is the major product when 2-methyl-2-butene reacts with $$HBr$$?

Accepted Answer

2-bromo-2-methylbutane

Question 8

Which of the following is the correct order of increasing acidity?

Accepted Answer

$$CH_4$$ \u003c $$NH_3$$ \u003c H_2O \u003c HF$$

Question 9

Which of the following reagents can convert an alkene to a vicinal diol?

Accepted Answer

$$OsO_4$$ followed by $$NaHSO_3$$

Question 10

A compound with the molecular formula $$C_4H_{10}O$$ can be classified as which of the following?

Accepted Answer

Alcohol or ether

Question 11

Which of the following statements is true regarding the SN2 reaction mechanism?

Accepted Answer

It proceeds with inversion of configuration at the reaction center.

Question 12

Which of the following is the correct product of the Diels-Alder reaction between 1,3-butadiene and ethene?

Accepted Answer

No reaction occurs

Question 13

Which of the following is the correct IUPAC name for the compound shown below?

$$CH_3CH_2CH(CH_3$)CH_2CH_3$$

Accepted Answer

3-methylpentane

Question 14

Which of the following statements about aromaticity is correct?

Accepted Answer

Aromatic compounds must have a planar ring and $$4n+2 pi $$electrons.

Question 15

Which of the following is the correct product when benzene reacts with $$Br_2 in $$the presence of $$FeBr_3$$?

Accepted Answer

Bromobenzene

Question 16

Which of the following is the correct structure for 2,2-dimethylpentane?

Accepted Answer

A five-carbon chain with two methyl groups on carbon 2

Question 17

Which of the following is the correct order of increasing nucleophilicity in polar aprotic solvents?

Accepted Answer

$$F^- \u003c Cl^- \u003c Br^- \u003c I^-$$

Question 18

Which of the following is the correct product when 1-butyne is treated with $$H_2$$ and Lindlar's catalyst?

Accepted Answer

cis-2-butene

Question 19

Which of the following statements is true about the Markovnikov rule?

Accepted Answer

The hydrogen atom adds to the carbon with more hydrogens.

Question 20

Which of the following is the correct product when cyclohexene reacts with $$KMnO_4 in $$cold, dilute solution?

Accepted Answer

cis-1,2-cyclohexanediol

Organic Chemistry Fundamentals: Concepts, Structures, and Nomenclature

Study Guide - Practice Questions