Deck 7: Bonding in Organic Molecules

Question 1

The octane number for gasoline is

A) the percentage of the gasoline that is alkanes with eight carbon.
B) the percentage of the gasoline that is 2,2,4 trimethyl pentane.
C) the percentage of the gasoline that is not heptane.
D) the percentage of the gasoline that is not heptane or hexane.
E) none of the above

Answer 1

E

Question 2

Naptha is

A) liquefied naphthalene.
B) a mixture of gases including methane, ethane, and propane.
C) a mixture of hydrocarbons with >C₂₀ used in asphalt.
D) a mixture of C₅-C₁₂ hydrocarbons used in gasoline.
E) the name for the boat conformation of cyclohexane.

Answer 2

D

Question 3

Increasing the chain length of straight chain alkanes causes the boiling point to increase because

A) the longer molecule assume a "balled up" shape.
B) the longer molecule assume a "stretched" shape.
C) the longer molecules have more dispersion forces.
D) the longer molecules have large dipole moments.
E) none of the above

Answer 3

C

Question 4

The C-C-C angle in cyclopropane must be

A) 45°
B) 60°
C) 90°
D) 109.5°
E) 120°

Question 5

Name the following compound.

A) 3-methyl-2-propylhexane
B) 4-methyl-6-propyl-2-hexene
C) 2-propyl-3-methyl-4-hexene
D) 4,5-dimethyl-2-octene
E) 4-pentyl-2-pentene

Question 6

Name the following compound.

A) 6,6,6-trimethyl-2-hexyne
B) 5,5,5-trimethyl-2-hexyne
C) 6,6-dimethyl-2-heptyne
D) 1,5,5,5-tetrametyl-1-pentyne
E) 5,5-dimethyl-2-hexyne

Question 7

Name the following compound.

A) 1-methylcyclopentane
B) 1-methylcyclohexane
C) 1-cylcopentylmethane
D) n-hexane
E) toluene

Question 8

The following molecule contains how many carbons with sp³ hybridization?

A) 2
B) 5
C) 6
D) 7
E) 8

Question 9

In C₆₀ each carbon is bonded to three other carbons. What is the hybridization of the carbons in C₆₀?

A) sp
B) sp²
C) sp³
D) 50% sp² and 50% sp³
E) the ones on the hexagonal faces are sp² and the pentagon faces are sp³

Question 10

The complete combustion of 1 mole of cyclobutanol into carbon dioxide and water will yield how many moles of water?

A) 1
B) 3.5
C) 4
D) 4.5
E) 9

Question 11

Oxidation of a primary alcohol will result in the formation of

A) a secondary alcohol.
B) an aldehyde.
C) a ketone.
D) a carboxylic acid.
E) an ester.

Question 12

Oxidation of an aldehyde will result in the formation of

A) a primary alcohol.
B) a secondary alcohol.
C) a ketone.
D) a carboxylic acid.
E) an ester.

Question 13

Which of the following molecules is chiral

A)

B)

C)

D)

E) none of the above

Question 14

The following compound is an

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

Question 15

In dimethyl ether, shown below, what would you predict for the C-O-C bond angle?

A) 109.5°
B) 180°
C) 120°
D) 105° (the same as water)
E) 110°

Question 16

The structure of DDT is given below. What is its molecular formula?

A) C₁₃H₉Cl₅
B) C₁₄H₉Cl₅
C) C₁₄H₈Cl₅
D) C₁₄Cl₅
E) C₁₃Cl₅

Question 17

The structure of acetaminophen is given below. How many chiral centers does the molecule have?

A) 0
B) 1
C) 2
D) 3
E) 8

Question 18

The molecule naphthalene is shown below. How would you describe the bonding in naphthalene using a mix of VB and MO?

A) 12 C-C s bonds (sp²-sp²), 12 C-H s bonds (sp²-1s), 6p MO's
B) 12 C-C s bonds (sp²-sp²), 10 C-H s bonds (sp²-1s), 6p MO's
C) 11 C-C s bonds (sp²-sp²), 11 C-H s bonds (sp²-1s), 5.5p MO's
D) 11 C-C s bonds (sp²-sp²), 8 C-H s bonds (sp²-1s), 5p MO's
E) 10 C-C s bonds (sp²-sp²), 10 C-H s bonds (sp²-1s), 5p MO's

Question 19

How many different isomers exist for Dichloro-ethene, C₂H₂Cl₂?

A) 0
B) 1
C) 2
D) 3
E) 4

Question 20

In the hydrogenation reaction of ethene a hydrogen is added to each carbon in the double bond. If trans-dichloroethene is reacted with H₂ how many isomers of dichloroethane are formed?

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

Question 21

Which would you expect to be most reactive?

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

Question 22

Why is there an energetic barrier to rotation of the C=C bond in ethene?

A) The trans isomer is more stable than the cis isomer.
B) Rotation breaks the s C-C bond.
C) Rotation breaks the p C-C bond.
D) Steric repulsion between the hydrogen atoms.
E) There is no energy barrier to rotation of this bond.

Question 23

Which of the following is a primary amines?

A)

B)

C)

D)

E)

Question 24

An amide bond is formed from the condensation of a carboxylic acid with a primary or secondary amine. What other product is formed in this reaction?

A) H₂
B) CO₂
C) NH₃
D) H₂O
E) there are no other products

Question 25

The structure of aspirin is shown below. What functional groups does aspirin possess?

A) ether
B) ester
C) carboxylic acid
D) aldehyde
E) a & b
F) b & c
G) a & c

Question 26

Benzene has a p electron system composed of the 6 pz orbitals on the carbon atoms? How many bonding and antibonding can be formed from these six atomic orbitals?

A) 6 bonding, 0 antibonding
B) 4 bonding, 2 antibonding
C) 3 bonding, 3 antibonding
D) 2 bonding, 4 antibonding
E) 6 bonding, 6 antibonding

Question 27

In a saturated hydrocarbon

A) the sample is all liquid.
B) the C-C bonds are all single bonds.
C) the oxygens are all in alcohol functional groups.
D) the double and triple C-C bonds are in the middle of the molecule.
E) the molecules are straight chains (no branching).

Question 28

Name the following compound.

A) o-dichloroxylene
B) o-dichlorobenezne
C) m-dichloroxylene
D) m-dichlorobenzene
E) p-dichloroxylene

Question 29

Which of the following functional groups does not contain a C-O double bond?

A) aldehyde
B) carboxylic acid
C) ester
D) ether
E) ketone

Question 30

How many p electrons are in C₇₀?

A) 0
B) 7
C) 35
D) 70
E) 140

Question 31

Which of the following is a tertiary alcohol?

A) n-butanol
B) isopropyl alcohol
C) 2-methyl-2-propanol
D) phenol
E) ethylene glycol

Question 32

Which of the following, when oxidized, will generally result in the formation of a ketone?

A) alkane
B) primary alcohol
C) secondary alcohol
D) tertiary alcohol
E) phenol

Question 33

Which of the following generally serves as chemical catalysts for biochemical reactions?

A) structural proteins
B) hormones
C) enzymes
D) carboxylic acids
E) all of the above