Deck 16: Organic Chemistry

Question 1

Which of the following structures represents the same molecule?

A) 1 and 2
B) 3 and 4
C) 2 and 3
D) 1 and 4
E) All of the structures show the same molecule

Answer 1

2 and 3

Question 2

Draw the structure of 3-bromo-2-methylhexane.

Answer 2

Question 3

The correct systematic name for the compound shown below would be:

A) 2,4-dimethylhexane
B) 4-ethyl-2-methylpentane
C) isopropylpentane
D) 2-methyl-4-ethylpentane
E) 2,3-dimethylhexane

Answer 3

2,4-dimethylhexane

Question 4

Ignoring stereochemistry, the correct systematic name for the compound shown below would be:

A) isooctene
B) 3-methyl-2,3-heptene
C) 4-ethyl-2-pentene
D) 3-methylheptane
E) 4-methyl-2-heptene

Question 5

The compound shown below is geraniol. It has a rose-like scent and occurs naturally in a number of flowers. What does the electron domain model predict the geometry to be around the carbon labeled 1?

A) linear
B) trigonal planar
C) tetrahedral
D) trigonal pyramidal
E) bent

Question 6

Which of the following best describes the relationship between the two structures shown below?

A) They represent the same compound.
B) They represent different compounds that are constitutional isomers.
C) They represent different compounds that are stereoisomers.
D) They represent different compounds that are alkenes.
E) They represent different compounds that are alkynes.

Question 7

Draw structures for all of the stable constitutional isomers of the formula C₄H₉Cl.

Question 8

Which of the following formulas represents an unsaturated hydrocarbon?

A) C₃H₈
B) C₃H₄
C) C₂H₄
D) C₅H₁₂
E) Both b and c are unsaturated hydrocarbons.

Question 9

What is the correct systematic name for the compound shown below?

A) 3-methyl-1-butyne
B) 3-methyl-1-butene
C) 2-methyl-3-butyne
D) isobutyne
E) 3,3-dimethyl-1-propyne

Question 10

A structure of the compound benzene (C₆H₆) is shown below. Are the carbon-carbon in benzene all the same length? Explain your answer.

Question 11

The molecule shown below is vanillin - one of the principle components of vanilla. Which of the following functional groups is not present in the structure of vanillin?

A) aldehyde
B) ether
C) alcohol
D) ketone
E) All of these functional groups are present

Question 12

The molecule shown below is Tamiflu () which is used to treat some types of influenza. Circle and identify each functional group present in Tamiflu.

Question 13

The compound shown below has an extremely strong smell of bananas. Which functional group is present in the molecule?

A) aldehyde
B) ketone
C) alkene
D) ester
E) ether

Question 14

The compound shown below is the over-the-counter analgesic acetaminophen. Which of the following functional groups are present in the molecule?

A) aldehyde
B) alcohol
C) amide
D) ester
E) Both alcohol and amide groups are present.

Question 15

The compound shown below is the stimulant amphetamine. Which functional group is present in the molecule?

A) amine
B) alcohol
C) amide
D) ester
E) Both alcohol and amide groups are present.

Question 16

In which of the following reactions is a carbon atom not oxidized or reduced?

A) CH₃CH₂Br + OH^- $\rightarrow$ CH₃CH₂OH + Br^-
B) CH₂=CHCH₃ + H₂ $\rightarrow$ CH₃CH₂CH₃
C) CH₃CH₃ + ½O₂(g) $\rightarrow$ CH₃CH₂OH
D) CH₃CH₂CHO + ½O₂(g) $\rightarrow$ CH₃CH₂CO₂H
E) A carbon atom is oxidized or reduced in all of these reactions.

Question 17

What is the oxidation number of the carbon shown in bold in the reactant and in the product?
CH₃CH₂CHO + ½O₂(g) $\rightarrow$ CH₃CH₂CO₂H

A) +3 in the reactant and +1 in the product.
B) 0 in the reactant and -2 in the product.
C) -2 in the reactant and 0 in the product.
D) +1 in the reactant and +3 in the product.
E) The carbon atom does not undergo a change in its formal oxidation state.

Question 18

What is the correct systematic name for the molecule shown below?

A) 1-butenol
B) 1-pentanol
C) 1-butanol
D) isobutanol
E) 1-hydroxybutane

Question 19

Which of the following is the conjugate base of ethanol (CH₃CH₂OH)?

A) CH₃CH₂OH₂⁺
B) CH₃CH₂O^-
C) CH₃CH₃
D) CH₄CH₂OH⁺
E) CH₃CH₂CO₂^-

Question 20

Which of the following alcohols would not be oxidized to the corresponding aldehyde or ketone?

A)
B)
C)
D)
E) All of the alcohols could be oxidized to the corresponding aldehyde or ketone.

Question 21

What is the most likely product of the reaction shown below?

Question 22

Arrange the following compounds in order from most acidic to least acidic. Explain your answer.

Question 23

Predict the products of the following reaction:

Question 24

The "fishy" odor in cooked fish, which is due to the presence of amines, can be reduced by the addition of lemon juice which contains citric acid. Explain.

Question 25

Which of the following best describes the relationship between the two structures shown below?

A) The represent the same compound.
B) The represent different compounds that are constitutional isomers.
C) The represent different compounds that are stereoisomers.
D) The represent different compounds that are alkanes.
E) They represent different compounds that are alkynes.

Question 26

Which of the following compounds would have a stereoisomer(s)?

A) 1 only
B) 2 only
C) 3 only
D) 2 and 3
E) 3 and 4

Question 27

The compound labeled 1 is geraniol. It has a rose-like scent and occurs naturally in a number of flowers. Compounds 2 and 3 are isomers of geraniol. Which statement is correct?

A) 2 is a constitutional isomer of geraniol and 3 is a stereoisomer.
B) 3 is a constitutional isomer of geraniol and 2 is a stereoisomer.
C) Both 2 and 3 are stereoisomers of geraniol.
D) Both 2 and 3 are constitutional isomer of geraniol
E) 2 and 3 are not isomers of geraniol.

Question 28

Which of the molecules shown below is chiral?

A)
B)
C)
D)
E) All of these compounds are chiral

Question 29

The molecule shown below is Tamiflu which is used to treat some types of influenza. Circle each carbon in the molecule that is a chiral center.

Question 30

One example of a Fisher-Tropsch reaction is shown below. Calculate the $\Delta$ H_rxn° using enthalpies of atom combination.
2CO(g) + 5H₂(g) $\rightarrow$ C₂H₆(g) + 2H₂O(g)
Is this reaction endothermic or exothermic?