Deck 2: Alkanes and Organic Nomenclature

Question 1

Consider the Newman projection. Give the systematic (IUPAC) name of this alkane.

Answer 1

This tests your ability to "decode" a Newman projection. Always remember that the "circle" represents only one carbon of a bond; there is a second carbon obscured behind it that you can't see-the one with the three bonds to the periphery. Hopefully you drew a structure before you constructed the name:
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The name then follows: 2,3-dimethylpentane.
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Question 2

Select all Newman projections that are valid Newman projections for stable conformations of butane. ("Stable" means located at any energy minimum in a plot of energy vs. dihedral angle.)
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Answer 2

A, B, and D. Projection B is a projection of the C1-C2 bond, whereas the other correct projections are projections of the C2-C3 bond. Projection C is not butane, and projection E is not a stable conformation of butane. Although the gauche conformation D is less stable than the anti conformation A, it lies at an energy minimum and certainly exists.
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Question 3

Consider the compound:
The largest substituent group mentioned (cited) explicitly in the name of this compound is

A) tert-butyl.
B) methyl.
C) ethyl.
D) propyl.
E) octyl.f.
some other group.

Answer 3

C

Question 4

Which one of the Newman projections is correct for the projected bond indicated by the arrow in 2,2,4-trimethylpentane?
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A)

B)

C)

Question 5

Consider the following alkane, shown in a skeletal structure. What is the IUPAC name of this compound?
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Question 6

Consider the alkane, shown in a skeletal structure. Which of the Newman projections depicts one of the staggered conformations of this compound about the projected bond (arrow) when viewed with the carbon marked with a * in the front?
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A)

B)

C)

D)

Question 7

Name the alkane using an IUPAC systematic name.

Question 8

Provide an IUPAC systematic name for this compound.
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Question 9

Consider the compound. This compound is a constitutional isomer of which unbranched alkane?

Question 10

Complete a Newman projection of the most stable conformation of this compound about the bond marked with the arrow. The carbon with the asterisk should be in front. You can use group abbreviations for large groups.
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Question 11

Which is a correct Newman projection of 3-methylpentane?

A)

B)

C)

Question 12

Which compound has the highest boiling point?

A)

B)

C)

D)

Question 13

Consider the IUPAC systematic name of the alkane.
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The name of this compound is

A) 5-ethyl-2-methyl-3-propylheptane.
B) 3-ethyl-5-isopropylnonane.
C) 6-ethyl-4-isopropyloctane.
D) 1,1-diethyl-3-isopropylhexane.
E) None of the above is a correct name.

Question 14

Complete the Newman projection on the right for the compound on the left, with the projection taken about the C3-C4 bond. The Newman projection should show the least stable staggered conformation.

Question 15

Behold the structure of vanillin, which is the main ingredient in vanilla extract.
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The functional groups in vanillin are best described as

A) a ketone, a phenol, and an ether.
B) an alcohol, an aldehyde, and an ether.
C) a ketone, an alcohol, and an ether.
D) a phenol, an aldehyde, and an ether.
E) an aldehyde, a phenol, and an alcohol.

Question 16

Identify the correct name for the compound.
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A) 1,1,1,4,4,4-hexamethylbutane
B) 1,2-di-tert-butylethane
C) 2,2,5,5-tetramethylhexane
D) some other name

Question 17

Behold the molecule hydroxyproline, drawn in its un-ionized form. Hydroxyproline is an important constituent (in combined form) of collagen. Which correctly describes the functional groups in hydroxyproline?
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A) alcohol, amine, carboxylic acid
B) alcohol, amide, carboxylic acid
C) amide, amine, carboxylic acid
D) ester, carboxylic acid, amine
E) None of these lists all of the functional groups correctly.

Question 18

The α-amino acid tyrosine has the following structure. What is the functional group (circled) in the side-chain of tyrosine?
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Question 19

Consider the structure of methyl acetate. Draw an alcohol that is a constitutional isomer. It may contain other functional groups.
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Question 20

The compound with the greatest boiling point is

A)

B)

C)

D)

Question 21

Give the systematic (IUPAC) name of this alkane.
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Question 22

Given the structure, classify each of the carbons as primary, secondary, tertiary, or quaternary.
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Question 23

Given the structure, classify each of the hydrogens as primary, secondary, or tertiary.
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Question 24

How many hydrogens are there in a noncyclic alkane containing 10 carbons?

Question 25

Draw the structure of 2-butyl-1,1-dimethylcyclohexane.