Deck 2: Alkanes: The Nature of Organic Compounds

Question 1

Label the following pair of compounds as:

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

Answer 1

B

Question 2

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

Answer 2

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

B

Question 4

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

Question 5

Provide the proper IUPAC name for the compound below.

Question 6

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 7

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 8

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 9

Circle and name each functional group in the following structure.

Question 10

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 11

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

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

Question 12

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 13

Provide a proper IUPAC name for the compound given below.

Question 14

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 15

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 16

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 17

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

Question 18

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 19

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

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

Question 20

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

Question 21

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

A)
B)
C)
D)

Question 22

Instructions: Label each pair of compounds below as:
Where stereoisomers are present, label the isomers as cis and trans.
Label:

Question 23

Which of the following cycloalkanes has the most ring strain?

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

Question 24

This skeletal structure corresponds to the molecular formula:

Question 25

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.

Question 26

Instructions: Label each pair of compounds below as:

Question 27

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 28

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

A)
B)
C)
D)

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

Draw two isomeric alcohols with the formula C₄H₁₀O.

Question 31

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 32

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 33

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

A)
B)
C)
D)

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 a tertiary chloride.

Question 35

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

A)
B)
C)
D)

Question 36

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 37

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 38

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.

Question 39

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 40

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 41

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 42

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.

Question 43

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 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?

Question 45

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