Deck 1: Structure and Bonding in Organic Molecules

Question 1

In the following molecule,how many carbon atoms are in the sp³ hybridization state?

A) 2
B) 4
C) 5
D) 6
E) 11

Answer 1

6

Question 2

Which of the following pairs are not resonance structures of each other?

A)

B)

C)

D)

E) All are pairs of resonance structures.

Answer 2

All are pairs of resonance structures.

Question 3

The lone-pair of electrons on nitrogen in the following molecule reside in what type of orbital?

A) sp³
B) sp²
C) sp
D) 2p
E) 2s

Answer 3

sp²

Question 4

In the following molecule,how many carbon atoms are in the sp² hybridization state?

A) 1
B) 3
C) 7
D) 8
E) 9

Question 5

The following molecule contains how many carbon atoms in the sp hybridization state?

A) 1
B) 3
C) 8
D) 13
E) 16

Question 6

What is the molecular formula of limonene,the major volatile compound in orange peel oil?

A) C₁₀H₁₈
B) C₁₀H₂₀
C) C₁₀H₁₆
D) C₁₁H₁₄
E) C₁₁H₁₈

Question 7

A positive charge on oxygen generally occurs when:

A) oxygen has too many electrons.
B) oxygen has too few electrons.
C) oxygen is sharing one of its non-bonding electron pairs.
D) oxygen has too many non-bonding electron pairs.
E) oxygen is borrowing electrons from another atom.

Question 8

What would be the ideal value for the indicated bond angle?

A) 120 $\degree$
B) 90 $\degree$
C) 104 $\degree$
D) 180 $\degree$
E) 109 $\degree$

Question 9

Which of the following is not a resonance structure of the others?

A)

B)

C)

D)

E)

Question 10

Which one of the following structures is not chemically identical to the others?

A)

B)

C)

D)

E)

Question 11

Which one of the following structures must be incorrect?

A)

B)

C)

D)

E)

Question 12

Which structure matches the following condensed structure?

A)

B)

C)

D)

E)

Question 13

The boxed item most likely represents what?

A) s orbital
B) sp³ orbital
C) p orbital
D) could be any of A-C
E) None of the above.

Question 14

In the following molecule,how many carbon atoms are in the sp² hybridization state?

A) 0
B) 1
C) 2
D) 4
E) 6

Question 15

How many atoms in ethene are required by sp² bonding to lie in the same plane?

A) 2
B) 3
C) 4
D) 5
E) 6

Question 16

Which one of the resonance structures below would be the most important (i.e.,most stable)?

A)

B)

C)

D)

E)

Question 17

The nitrogen of trimethylamine [(CH₃)₃N] contains how many lone pairs of electrons?

A) none
B) one
C) two
D) three
E) there is no nitrogen in this molecule

Question 18

Of those indicated,which would be the shortest carbon-carbon bond in $\alpha$ -selinene?

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

Question 19

In the following molecule,how many carbon atoms are in the sp hybridization state?

A) 2
B) 4
C) 6
D) 12
E) None of the above.

Question 20

How many hydrogen atoms are part of the following steroid?

A) 18
B) 20
C) 21
D) 22
E) 24

Question 21

What is the molecular formula of carvone,the major volatile compound in caraway oil?

A) C₁₀H₁₈O
B) C₁₀H₁₇O
C) C₁₀H₁₆O
D) C₁₀H₁₄O
E) C₁₀H₁₅O

Question 22

Which one of the following structures must be incorrect?

A)

B)

C)

D)

E)

Question 23

Which of the carbon-carbon bonds indicated would you expect to be the longest in stilbene?

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

Question 24

The molecular formula for piperitone is

A) C₉H₁₆O
B) C₁₀H₁₈O
C) C₉H₁₈O
D) C₁₀H₁₄O
E) C₁₀H₁₆O

Question 25

In the following molecule,how many carbon atoms are in the sp³ hybridization state?

A) 2
B) 4
C) 5
D) 6
E) 9

Question 26

Which structure is different from the others?

A)

B) CH₃CHClCH(CH₃)₂
C)

D)

E) All are identical.

Question 27

Of those indicated,which would be the shortest carbon-carbon bond in $\beta$ -cadinene?

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

Question 28

Which of the following pairs are not resonance structures of each other?

A)

B)

C)

D)

E) All are pairs of resonance structures.

Question 29

Which of the following molecules are most likely to be held together by a purely covalent bond?

A) NaCl
B) H₂
C) HF
D) BH₃
E) KI

Question 30

What would be the ideal value for the indicated bond angle?

A) 120 $\degree$
B) 90 $\degree$
C) 104 $\degree$
D) 180 $\degree$
E) 109 $\degree$

Question 31

Which structure matches the following condensed structure?

A)

B)

C)

D)

E)

Question 32

The following molecule has what molecular formula?

A) C₃₉H₅₈O
B) C₄₀H₅₈O
C) C₃₉H₆₀O
D) C₄₄H₄₄O
E) None of the above.

Question 33

Which of the following statements are true of sp orbitals?

A) Orbitals of the sp type are 50% s and 50% p character.
B) They are hybrid orbitals.
C) They are linear.
D) They result when one s orbital and one p orbital are mixed.
E) All are correct.

Question 34

The carbon atom in CH₂Cl₂ has what hybridization?

A) sp
B) sp²
C) sp³
D) sp⁴
E) they are not hybridized

Question 35

How many sp² hybridized carbon atoms are in the potent anticancer compound hydroxymethylacylfulvene?

A) 2
B) 4
C) 6
D) 8
E) None of the above.

Question 36

What is the molecular formula of camphor?

A) C₁₀H₁₅O
B) C₁₀H₁₆O
C) C₁₀H₁₇O
D) C₁₁H₁₈O
E) C₁₁H₁₆O

Question 37

A fairly common algal metabolite is the compound (-)-geosmin,which imparts a musty odor to water even at concentrations in the ppb range.What is the molecular formula of geosmin?

A) C₁₁H₂₀O
B) C₁₂H₂₂O
C) C₁₁H₂₁O
D) C₁₂H₂₀O
E) C₁₂H₂₁O

Question 38

Camptothecin is an important anticancer compound; how many carbons are in the sp hybridization state?

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

Question 39

The process of adding electrons one by one to atomic orbitals beginning with the lowest energy is described by:

A) the Aufbau Principle.
B) Hund's Rule.
C) the de Broglie Relation.
D) the Pauli Exclusion Principle.
E) Coulomb's Law.

Question 40

How many sp³ carbons are in the following molecule?

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

Question 41

Which of the following cannot be a correct Lewis structure?

A)

B)

C)

D)

E) All are correct.

Question 42

The following molecule belongs to a class of compounds known as allenes.Based on your knowledge of bonding,predict the hybridization of the carbon atom indicated by the arrow.

A) sp
B) sp²
C) sp³
D) p-p pi
E) a hypervalent carbon

Question 43

A hydrocarbon with a double bond and a ring will have the general formula?

A) C_nH_2n+2
B) C_nH_2n
C) C_nH_2n-2
D) C_nH_2n-4
E) C_2nH_2n

Question 44

Which of the following represent resonance contributing Lewis structures for CH₂N₂?

A)

B)

C)

D)

E) both A and B are correct

Question 45

Which of the following most correctly defines "structural isomers"?

A) molecules with different molecular formulas but the same connectivity
B) compounds that are not constitutional isomers
C) molecules with the same molecular formula but different connectivity
D) Anti and gauche conformers
E) both B and C

Question 46

How many structural isomers exist for the formula C₆H₁₄?

A) 3
B) 4
C) 5
D) 6
E) 7

Question 47

How many isomers of C₅H₁₂ are possible?

A) two
B) three
C) four
D) five
E) six

Question 48

How many different resonance structures can be drawn for the benzyl cation (shown below)which place the plus charge on a carbon atom in the ring?

A) 1
B) 2
C) 3
D) 5
E) 6

Question 49

How many isomers of C₄H₉Br are possible?

A) two
B) three
C) four
D) five
E) six

Question 50

What is the hybridization of the each of the labeled atoms for the potent neurotoxin (-)-gephyrotoxin?

A) A = sp²,B = sp,C = sp²,D = sp³,E = sp³
B) A = sp²,B = sp,C = sp³,D = sp³,E = sp²
C) A = sp²,B = sp,C = sp²,D = sp³,E = sp²
D) A = sp²,B = sp,C = sp³,D = sp³,E = sp³
E) A = sp,B = sp,C = sp³,D = sp³,E = sp³