Organic Chemistry-Chapter 1 Testbank

Chapter One MULTIPLE CHOICE QUESTIONS

Topic: General Section: 1.1 Difficulty Level: Easy 1. Credit for the first synthesis of an organic compound from an inorganic precursor is usually given to: A) Berzelius B) Arrhenius C) Kekule D) Wohler E) Lewis Ans: D Topic: Atomic Orbitals, Hybridization Section: 1.2 Difficulty Level: Easy 2. A) B) C) D) E)

3

How many sigma 1s-2sp bonds are there in ethane? 7 6 5 3 1 Ans: B

1

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Topic: Isomerism Section: 1.3 Difficulty Level: Easy 3. Which of the following is a set of constitutional isomers? Br Br

I A) B) C) D) E)

Br

II

Br

III

IV

I and II II and and III I, II, and III II, III, and IV I, III, III, and and IV Ans: E

Topic: Isomerism Section: 1.3 Difficulty Level: Easy 4. A) B) C) D) E)

CH3CH2OCH2CH3 and CH3CH2CH2CH2OH are examples of what are now termed: Structural isomers Resonance structures structur es Functional isomers Empirical isomers Constitutional isomers Ans: E















Topic: Isomerism Section: 1.3 Difficulty Level: Easy 5. Which of the following structures represent compounds that are constitutional isomers of each other?

I

A) B) C) D) E)

II

III

IV

I and II I and III I, II, and III I, II, III, III, and and IV II and III Ans: C

Topic: Isomerism Section: 1.3 Difficulty Level: Easy 6. Which compound is not a constitutional constitutional isomer of the others? N

O

I A) B) C) D) E)

N

O

N

O

II

O

H N

III

I II III IV All of the above are isomers of each other. Ans: D

IV















Topic: Isomerism Section: 1.3 Difficulty Level: Easy 7.

A) B) C) D) E)

Consider the following: CH3CH2CH=CHCH2CH3 I

CH3CH2CH2CH2CH=CH2 II

CH3CH=CHCH2CH2CH3 III

CH2=CHCH2CH2CH2CH3 IV

Which two structures represent the same compound? I and II II and and III I and III II and and IV None of these Ans: D

Topic: Isomerism Section: 1.3 Difficulty Level: Easy 8. Which of the following represent a pair pair of constitutional isomers? A) and B) CH3CH=CH2 and CH2=CHCH3 Br Br C) Br

H

H

and Br

H Br

D)

H Br H

Br

and

H

H

H

E) More than one of these Ans: E

Br















Topic: Isomerism Section: 1.3 Difficulty Level: Easy 9. Which of the following represent pairs pairs of constitutional constitutio nal isomers? isomers? OH O A) O

and

O

CH3

B)

CH3 Br

H

H

and Br

H CH2

C) Br

H Br

CH3

and

H

H

CH3

D) None of these pairs pairs E) All of these pairs Ans: D Topic: Isomerism Section: 1.3 Difficulty Level: Medium 10. Which compound is not a constitutional constitutional isomer of the others? OH

O O

OH

I A) B) C) D) E)

II

III

I II III IV All of the above are isomers of each other. Ans: A

IV















Topic: Isomerism Section: 1.3 Difficulty Level: Medium 11. Which compound is not a constitutional constitutional isomer of the others? Br

Br

Br Br

Br

A) B) C) D) E)

I II III IV I and II II III IV and V All of the above are isomers of each other. Ans: C

V

Topic: Atomic Orbitals, Periodic Trends, Electronegativity Section: 1.4 Difficulty Level: Easy 12. A) B) C) D) E)

The greatest degree of ionic ionic character is anticipated for the bond bond between: H and C H and Cl C and Cl H and Br Br and Cl Ans: B

Topic: Periodic Trends, Electronegativity Section: 1.4 Difficulty Level: Easy 13. A) B) C) D) E)

Select the least least electronegative element from the list list below: P N Mg Si K Ans: E

















Topic: Periodic Properties, Electronegativity Section: 1.4A Difficulty Level: Easy 14. A) B) C) D) E)

Select the most most electronegative element from the list list below: H O N B C Ans: B

Topic: Lewis Structures Section: 1.5 Difficulty Level: Medium 15. Which of the following following is the Lewis structure for CH3CH2O2H? H H A) H

B) H

C

C

O

H H

H

C

O

C

H

O

H

C

C

O

H H

H

C

O

H H

H

O

H

O

H

H

H

C) H

D) H

E)

H

H C H

O

H

















Topic: Lewis Structures Section: 1.5 Difficulty Level: Medium 16. A) B) C) D) E)

In which of the following does the central atom have 2 pairs pairs of non-bonding electrons? O3 CO2  CO3  NH4 H2 S Ans: E

Topic: Lewis Structures, Formal Charges Section: 1.5 Difficulty Level: Medium 17. Which is NOT a correct Lewis structure? struct ure? .. A) H N F: .. H H

B)

.. H

C) H D) H

F:

C

..

..

H

..

O

O

..

.. O ..

..

H

.. :O H

B

:O H .. E) None of these Ans: A

















Topic: Lewis Structures, Formal Charges Section: 1.5 Difficulty Level: Medium -

18. Which of these is is a correct electron-dot representation of the nitr nitrite ite ion, NO2 ? .. .. .. .. .. .. .. :O:N::O :O::N::O :O::N:O: .. .. .. .. .. .. I

A) B) C) D) E)

III

II .. .. .. :O:N:O: .. ..

.. .. .. :O::N:O .. ..

IV

V

I II III IV V Ans: A

Topic: Lewis Structures Section: 1.5 Difficulty Level: Hard 19. Which of the following following is the Lewis structure for CH3CO2H? H H A) H

B) H

C

C

H H

H O

C

C

O

O

O

H

H

















Topic: Lewis Structures Section: 1.5 Difficulty Level: Hard 20. Considering Lewis structures, which of these compounds possesses a single single unpaired electron? A) N2 B) N2O C) NO D) N2O4 E) O2 Ans: C Topic: Lewis Structures Section: 1.5 Difficulty Level: Hard ..

21.

Z Y

A) B) C) D) E)

..

Y is a generalized structural representation which can be used for all of the

following, except: OF2 – NH2 H2 S BeBr2 There is is no no exception. Ans: D

Topic: Lewis Structures, Formal Charges Section: 1.6 Difficulty Level: Easy 22. Expansion of the valence valence shell to accommodate more than eight electrons is possible with:

















Topic: Lewis Structures, Formal Charges Section: 1.7 Difficulty Level: Easy 23. What is the formal formal charge on oxygen in in the following structure? H3CC

A) B) C) D) E)

O

+2 +1 0 -1 -2 Ans: B

Topic: Lewis Structures, Formal Charges Section: 1.7 Difficulty Level: Easy 24. What is the formal formal charge on carbon in the following structure? Cl

A) B) C) D) E)

C

Cl

+2 +1 0 -1 -2 Ans: C

Topic: Lewis Structures, Formal Charges Section: 1.7 Difficulty Level: Easy 25. In which structure(s) struct ure(s) below does the oxygen have a formal charge of +1?



















Topic: Lewis Structures, Formal Charges Section: 1.7 Difficulty Level: Easy 26. Which structure(s) contain(s) an oxygen that bears a formal charge of +1? .. .. :O :O .. .. .. .. : O C O: H C H3C O H H3C O CH3 C :O: : O: : O: .. .. .. H CH3 I

A) B) C) D) E)

II

III

IV

V

I and II III and and IV V II I and V Ans: B

Topic: Lewis Structures, Formal Charges Section: 1.7 Difficulty Level: Easy 27. Which of the following molecules or ions has a nitrogen with a formal charge of -1?



















Topic: Lewis Structures, Formal Charges Section: 1.7 Difficulty Level: Easy 28. In which structure(s) struct ure(s) below does nitrogen nitrogen have a formal charge of +1? H3C

N

CH2

H3C

.. N

..

H H

.. N

H

.. .OH .

.. H3C

NH2

H

I

A) B) C) D) E)

H3C

.. N

CH3

II

III

IV

I II and and IV III and and V I and V V Ans: A

Topic: Lewis Structures, Formal Charges Section: 1.7 Difficulty Level: Easy 29. Which of the following following is an ion with with a single negative charge? .. A) H C O:

V

CH3



















Topic: Lewis Structures, Formal Charges Section: 1.7 Difficulty Level: Easy 30. What is the formal formal charge on oxygen in in the following structure? .. H3 C

O

CH3

CH3

A) B) C) D) E)

+2 +1 0 -1 -2 Ans: B

Topic: Lewis Structures, Formal Charges Section: 1.7 Difficulty Level: Easy 31. Listed below are electron dot formulas for for several simple molecules and ions. All valence electrons are shown; however, electrical charges have been omitted deliberately.



















Topic: Lewis Structures, Formal Charges Section: 1.7 Difficulty Level: Easy 32. Listed below are electron dot formulas for for several simple molecules and ions. All valence electrons are shown; however, electrical charges have been omitted deliberately.

A) B) C) D) E)

H : Be : H

H .. H:B:H .. H

H .. H:N:H ..

H .. H:N:H .. H

H .. H:O:H ..

I

II

I II

IV

V

Which of the structures is negatively charged? I II III IV V Ans: B

Topic: Lewis Structures, Formal Charges



















Topic: Lewis Structures, Formal Charges Section: 1.7 Difficulty Level: Medium 34. In which of these cases does the central atom have a zero formal charge? A) HFH H B) H3 C O F C) F

B

CH3

F

F H

D) H3C

N

CH3

H CH3

E) H3C

C

CH3

CH3

Ans: E Topic: Lewis Structures, Formal Charges Section: 1.7





















Topic: Atomic Orbitals, Lewis Structures, Resonance Section: 1.8 Difficulty Level: Easy 36. Which of the following pairs are NOT resonance structures? A) H3C

:

:

O

N

:

O:

and

H3C

:

:

O

N

:

B)

: . .

O

O

and

. .

: . .

O

. .

C

: O . .

.

C) H3C

:

:

O

N

:

O: :

:

C

:

:

O:

and

H 3C

.

O

.

O

. .

N .

:

. .





















Topic: Resonance Section: 1.8 Difficulty Level: Medium 38. Which of the following following species is a resonance form of the species in the box? P(CH3)2

N H

P(CH3)2

N H

N H

I

A) I B) II C) III

P(CH3)2

P(CH3)2

N H

II

P(CH3)2

N H

III

IV





















Topic: Resonance Section: 1.8 Difficulty Level: Medium 40. Which of the following species is not a resonance form of the following species? O

A) O

B) O





















Topic: Resonance Section: 1.8 Difficulty Level: Medium 42. Which of the following species is/are not a resonance form(s) of the species in the box?

I

A) I

II

III

IV





















Topic: Resonance Section: 1.8 Difficulty Level: Medium 44. Which of the following species is/are not a resonance form(s) of the species in the box?

N

N

N

I

A) I and II B) II and and III C) III and IV

N

II

N

III

IV























Topic: Resonance Section: 1.8 Difficulty Level: Medium 46. Which of the following following species contr contributes ibutes more to the overall hybrid for the species in























Topic: Resonance Section: 1.8 Difficulty Level: Hard 48. Which of the following following species is a resonance form of the following species?























Topic: Resonance Section: 1.8 Difficulty Level: Hard 49. Which of the following structures structur es is/are not a resonance form of the following species?























Topic: Resonance Section: 1.8 Difficulty Level: Hard 50. Which of the following following species are resonance forms of the species in in the box? box?























Topic: Resonance Section: 1.8 Difficulty Level: Hard

































































































































































































































































































































































































Organic Chemistry-Chapter 1 Testbank

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