Deck 2: Alkanes: the Nature of Organic Compounds

Question 1

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

Answer 1

Question 2

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

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

Answer 2

5

Question 3

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 3

both a and c

Question 4

Provide a proper IUPAC name for the compound given below.

Question 5

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 6

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 7

Provide the proper IUPAC name for the compound below.

Question 8

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

Question 9

Instructions: Refer to the structure below to answer the following question(s).
Refer to instructions. Which groups have a 1,3-diaxial interaction with each other?

Question 10

Draw and name the seven constitutional isomers for cycloalkane, C₆H₁₂.

Question 11

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 12

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 13

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

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

Question 14

Instructions: Refer to the structure below to answer the following question(s).
Refer to instructions. Which of the labeled groups in the structure are equatorial?

Question 15

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 16

Instructions: Refer to the structure below to answer the following question(s).
Refer to instructions. Which of the labeled groups is trans to b?

Question 17

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

Question 18

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 19

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

Question 20

Label the following pair of compounds as:

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

Question 21

Instructions:
MATCH a structure below to each of the following descriptions and place the letter corresponding to the structure in the blank.
Refer to Instructions. _______is an amino aldehyde.

A)
B)
C)
D)
E)
F)
G)

Question 22

Draw a structure corresponding to the following name:
cis-1-sec-butyl-2-ethylcyclopentane

Question 23

Draw two isomeric alcohols with the formula C₄H₁₀O.

Question 24

Which of the following structures represents trans-1,2-dimethylcyclohexane?

A)
B)
C)
D)

Question 25

This skeletal structure corresponds to the molecular formula:

A) C₅H₆O₆
B) C₇H₁₀O₆
C) C₆H₆O₆
D) C₆H₈O₆

Question 26

Substitution of which of the following groups on a cycloalkane would result in the greatest amount of steric strain?

A) bromo
B) ethyl
C) isopropyl
D) hydroxyl

Question 27

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

A)
B)
C)
D)

Question 28

Instructions:
MATCH a structure below to each of the following descriptions and place the letter corresponding to the structure in the blank.
Refer to Instructions. _____is a cyclic alkane with two cis methyl groups.

A)
B)
C)
D)
E)
F)
G)

Question 29

Instructions: (-)-Menthol is responsible for the characteristic flavor and taste of peppermint. The structure of (-)-menthol is shown below. Use this information to answer the following question.

-Refer to instructions. On the chair template provided below, draw the two chair conformations that are in equilibrium for (-)-menthol.

Question 30

Instructions: For each disubstituted cyclohexane below, draw its ring-flip isomer. Circle the most stable conformation and label the substituent groups as axial or equatorial.
Draw and label:

Question 31

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

A)
B)
C)
D)

Question 32

In which of the following compounds would the carbon-carbon bond angle diverge the greatest from 109 $\degree$ ?

A) cyclodecane
B) cyclooctane
C) cyclopentane
D) cyclopropane

Question 33

Instructions: (-)-Menthol is responsible for the characteristic flavor and taste of peppermint. The structure of (-)-menthol is shown below. Use this information to answer the following question.

-D-Pinitol is an interesting hexahydroxycyclohexane, whose structure is shown below. On the templates provided, draw the two chair conformations that are in equilibrium for D-pinitol. Circle the most stable conformation.

Question 34

Instructions:
MATCH a structure below to each of the following descriptions and place the letter corresponding to the structure in the blank.
Refer to Instructions. _____is an aromatic ketone.

A)
B)
C)
D)
E)
F)
G)

Question 35

Instructions: For each disubstituted cyclohexane below, draw its ring-flip isomer. Circle the most stable conformation and label the substituent groups as axial or equatorial.
Draw and label:

Question 36

Instructions: Label each pair of compounds below as:

A)identical
B)stereoisomers
C)constitutional isomers
D)identical, but differing in conformation
Where stereoisomers are present, label the isomers as cis and trans.
Label:

Question 37

Instructions:
MATCH a structure below to each of the following descriptions and place the letter corresponding to the structure in the blank.
Refer to Instructions. _____is a tertiary chloride.

A)
B)
C)
D)
E)
F)
G)

Question 38

Which of the following cycloalkanes has the most ring strain?

A) cyclopropane
B) cyclobutane
C) cyclopentane
D) cyclohexane

Question 39

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

A)
B)
C)
D)

Question 40

Instructions: Label each pair of compounds below as:

A)identical
B)stereoisomers
C)constitutional isomers
D)identical, but differing in conformation
Where stereoisomers are present, label the isomers as cis and trans.
Label:

Question 41

Instructions:
Consider the conformations of 2-methylbutane shown below to answer the following questions.
Refer to Instructions. Which of the structures represents the most stable conformation of 2-methylbutane?

Question 42

Instructions:
Consider the conformations of 2-methylbutane shown below to answer the following questions.
Draw the Newman projection for the specified conformations for rotation about the C-C bond of 1,2-dichloroethane.
There are two eclipsed conformations of 1,2-dichloroethane. Draw them.

Question 43

Instructions:
Consider the conformations of 2-methylbutane shown below to answer the following questions.
Draw the Newman projection for the specified conformations for rotation about the C-C bond of 1,2-dichloroethane.
There are two staggered conformations of 1,2-dichloroethane. Draw them.

Question 44

Instructions:
Consider the conformations of 2-methylbutane shown below to answer the following questions.
Refer to Instructions. Which of the structures represents the least stable conformation of 2-methylbutane?