Deck 3: Organic Compounds: Alkanes and Their Stereochemistry

Question 1

Which hydrogen atom(s) in the following compound is (are) classified as tertiary?

A) a
B) b
C) c
D) both a and c
E) There are no tertiary hydrogen atoms.

Answer 1

b

Question 2

Circle and name each functional group in the following structure. cortisone acetate (active ingredient in steroid skin cream)

Answer 2

Question 3

Draw the structure of a five carbon ketone containing one tertiary carbon atom.

Answer 3

Question 4

Experiments have shown that for 1,2-dichloroethane, ClCH₂CH₂Cl, in tetrachloromethane solution at 25° C, 70% of the molecules are in the anti and 30% are in the gauche conformation. Use this information to answer the following question(s).
Refer to instructions. Draw a Newman projection of the highest energy eclipsed conformation of 1,2-dichloroethane.

Question 5

Provide the line bond structure for 4-(2,2-dibromoethyl)-3,5-dichloroheptane.

Question 6

Match the Newman projection for the conformation of 2-methylbutane to the indicated position on the potential energy diagram. A B C D
Refer to instructions. Conformations A and D are represented by the Roman numerals _____ and _____ in the diagram, respectively.

Question 7

One of the functional group classifications is characterized by the presence of an sp² hybridized carbon atom. This functional group could be:

A) alkyl halide
B) sulfide
C) alcohol
D) aldehyde
E) alkyne

Question 8

The carbon atoms within the functional group of the following classifications are: alkene ester carboxylic acid amide

A) sp
B) sp²
C) sp³
D) sp² and sp³

Question 9

Which of the following functional group classifications do not contain oxygen?

A) ether
B) thiol
C) aldehyde
D) ester
E) amide

Question 10

Provide a proper IUPAC name for the compound given below.

Question 11

Match the Newman projection for the conformation of 2-methylbutane to the indicated position on the potential energy diagram. A B C D
Refer to instructions. Conformations B and C are represented by the Roman numerals _____ and _____ in the diagram, respectively.

Question 12

Among the following structures, how many different compounds are represented?

A) 5
B) 4
C) 3
D) 2
E) 1

Question 13

If ethane reacts with a large excess of chlorine over a long period of time, the most likely major product of the reaction would be:

A) CCl₃CCl₃
B) CH₃CH₃
C) CH₂ClCH₂Cl
D) CH₂ClCH₃
E) Ethane does not react with the halogens.

Question 14

To which functional group classification does the following molecule belong?

A) ester
B) ketone
C) alcohol
D) carboxylic acid
E) both b and c

Question 15

Experiments have shown that for 1,2-dichloroethane, ClCH₂CH₂Cl, in tetrachloromethane solution at 25° C, 70% of the molecules are in the anti and 30% are in the gauche conformation. Use this information to answer the following question(s).
Refer to instructions. Draw a Newman projection of the anti conformation of 1,2-dichloroethane.

Question 16

Experiments have shown that for 1,2-dichloroethane, ClCH₂CH₂Cl, in tetrachloromethane solution at 25° C, 70% of the molecules are in the anti and 30% are in the gauche conformation. Use this information to answer the following question(s).
Refer to instructions. Draw a Newman projection of the gauche conformation of 1,2-dichloroethane.

Question 17

4-ethyl-3,3,4-trimethylheptane could be classified as:

A) an alkane
B) saturated
C) aliphatic
D) a paraffin
E) all of these

Question 18

4-ethyl-3,3,4-trimethylheptane contains:

A) two quaternary carbon atoms
B) two tertiary carbon atoms
C) four secondary carbon atoms
D) a and c
E) all of these

Question 19

Label the following pair of compounds as:

A) identical
B) constitutional isomers
C) stereoisomers
D) unrelated

Question 20

Provide a line bond structure for 5-tert-butyl-2,3-dimethyloctane.

Question 21

The most stable conformation of an alkane occurs when

A) carbon−carbon bonds are staggered and bulky groups are gauche.
B) carbon−carbon bonds are staggered and bulky groups are anti.
C) carbon−carbon bonds are eclipsed and bulky groups are gauche.
D) carbon−carbon bonds are eclipsed and bulky groups are anti.

Question 22

Which of the following Newman projections represents the most stable conformation of 2,3-dimethylbutane? ​
A B C D ​

A) A
B) B
C) C
D) D

Question 23

Name these groups (left to right). where represents the parent chain.

A) sec-propyl, sec-butyl, isobutyl
B) isopropyl, isobutyl, sec-butyl
C) sec-propyl, tert-butyl, isobutyl
D) isopropyl, tert-butyl, isobutyl
E) isopropyl, tert-butyl, sec-butyl

Question 24

Which of the following alkanes is the most likely to be a liquid at room temperature?

A) propane
B) butane
C) pentane
D) hexane

Question 25

Choose a correct IUPAC name for:

A) 3-methyl-l-tert-butylhexane
B) 5-methyloctane
C) 2,5-dimethylheptane
D) 4,7,7-trimethyloctane
E) none of these

Question 26

Consider the conformations of 2-methylbutane shown below to answer the following question(s).
A B C D a.​A
b.​B
c.​C
d.​D
Which of the structures represents the most stable conformation of 2-methylbutane?

Question 27

What is the IUPAC name of the following compound?

A) 2-ethyl-4-methylpentane
B) 2,4-dimethylhexane
C) 3,5-dimethylhexane
D) 1,1,3-trimethylpentane

Question 28

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

A) 3
B) 4
C) 5
D) 8

Question 29

Consider the conformations of 2-methylbutane shown below to answer the following question(s).
A B C D a.​A
b.​B
c.​C
d.​D
Which of the structures has two gauche interactions?

Question 30

Pick the set of terms that correctly classifies the compound.

A) tertiary amine, primary alkyl chloride, secondary alcohol
B) primary amine, primary alkyl chloride, secondary alcohol
C) primary amine, primary alkyl chloride, tertiary alcohol
D) secondary amine, primary alkyl chloride, secondary alcohol
E) secondary amine, secondary alkyl chloride, secondary alcohol

Question 31

Designate each carbon as primary, secondary, tertiary, or quaternary.

Question 32

Which of the following Newman projections does not represent 2-methylhexane? ​
A B C D ​
​
​

A) A
B) B
C) C
D) D