CHE 275

STRUCTURE AND BONDING

CHAP 1 ASSIGN

1. Which pair of elements would form an ionic bond?

A. H and F

B. H and C

C. S and N

D. Li and F

2. For the bond-line structure in the box below, select the condensed formula that corresponds to it.
A. CH3CH2(OH)CH2(CH3)(CH2)2C(CH3)3
B. CH2(OH)CH(CH3)(CH2)2CH3
C. CH3CH(OH)(CH2)3C(CH3)3
D. CH3CH(OH)CH(CH3)(CH2)2CH3
E. CH3CH(OH)CH(CH3)(CH2)2C(CH3)3
3. Select the pair of structures which represent correctly drawn contributing resonance forms.

A.

B.

C.

D.

E.
4. The oxygen atom of a ketone (such as cyclohexanone) contains 2 lone pairs of electrons. These pairs of electrons most
likely reside in what type of orbital?
A.
B.
C.
D.
E.

s orbital
p orbital
sp3 orbital
sp2 orbital
sp orbital

5. Which of the following structures is correctly represented by the molecular formula: C 8H10O2?

6. The compound shown below [2-(4'-methoxyphenyl)-3-(3",4",5"-trimethoxybenzoyl)-6-methoxybenzo[b]thiophene] is a

novel chemotherapeutic agent which functions by inhibiting tubulin polymerization. How many carbon atoms are sp2
hybridized in this molecule?
A.
B.
C.
D.
E.

No carbon atoms are sp2 hybridized in this molecule.

Twenty-one carbon atoms are sp2 hybridized.
Two carbon atoms are sp2 hybridized.
Eighteen carbon atoms are sp2 hybridized.
Twenty carbon atoms are sp2 hybridized.

7. What would be the bond-line structure that corresponds to (CH3)2CHCH2CH2C6H5?

A.

B.

C.

D.

E.
8. How many carbon atoms are sp hybridized in the following molecule?
A.
B.
C.
D.
E.

0 carbon atoms are sp hybridized.

2 carbon atoms are sp hybridized.
3 carbon atoms are sp hybridized.
6 carbon atoms are sp hybridized.
11 carbon atoms are sp hybridized.

9. What bond angles would you expect to have around

the indicated carbon?
A.
B.
C.
D.
E.

130
120
109
90
60

10. What is the molecular formula of the molecule shown below?

A.
B.
C.
D.
E.

C10H10O
C9H10O
C9H8O
C9H9O
C9H11O
2

11. The condensed formula (CH3)3CCH2CH(OH)C6H5 is represented by which of the following bond-line structures?

A.

B.

C.

D.

E.
12. Which of the following represent a pair of constitutional isomers?

and

A.

Br

Br
Br

H
C.

B. CH3CH=CH2 and CH2=CHCH3

Br

and Br

Br
H

Br

and

D.

Br

E. More than one of these. Which ones?

13. Which of the following is not a conjugate acid - conjugate base pair (in that order)?
A. H3PO4, H2PO4
C. CH3CH2OH, CH3CH2O
E. HPO4, H2PO4
14. Consider the equilibrium:

B. HBF4, BF4
D. H3O+, H2O

PO43+ H2OP

Which are the Brnsted-Lowry bases?

A. PO43 and HPO4
C. PO43 and H2O
E. H2O and HPO42

B. PO43 and OH
D. H2O and OH

15. Convert the skeletal drawing of the following

pharmaceutical into a molecular formula.

CH3SO2

16. With regard to contributing structures, which of the following statements is true?
A.
B.
C.
D.
E.

Contributing structures undergo rapid interconversion.

No more than one atom may change connectivity between valid contributing structures.
In determining contributing structures, only electrons and charge may change location.
Contributing structures impart instability to a molecule.
Only two contributing forms may exist for any one molecule.
3

17. What is the charge (from left to right) on each of the species below?

A. +1, 1, 1, 0

B. 1, 0, +1, 0

C. 0, +1, +1, 0

D. +1, 0, +1, 0

18. Welwistatin (shown below) is a structurally interesting, newly discovered cytotoxic agent. How many hydrogen atoms are
contained in welwistatin?
A.
B.
C.
D.
E.

20 hydrogen atoms
19 hydrogen atoms
18 hydrogen atoms
13 hydrogen atoms
10 hydrogen atoms

19. Which hydrogen in the following molecule would you expect to be the most acidic (i.e., most easily removed as H+)?

A.

B.

C.
E. None of these can be considered acidic.

D.

20. In the compound sodium methoxide (NaOCH3), there is __________ bonding.

A.. ionic
C. nonpolar covalent
E. resonance stabilized

B. polar covalent
D. a mixture of ionic and covalent

21. For each of the following three bonds, specify whether the negative end of the dipole is towards the left or the right.
CBr
A
A. A-left, B-left, C-no dipole
C. A-right, B-left, C-no dipole

ClH
B

HH
C

B. A-left, B-right, C-no dipole

D. one cannot decide unless all other attached elements are given

22. Which structure and formal charge distribution is correct for diazaomethane, CH 2N2?

23. Which of the following species have no formal charge on their carbon atom?

A. A, C

B. A, D

C. B, C

D. B, D

24. The formal charges on nitrogen and the starred oxygen atom of the compound show below are
A. N +1; O* 0
B. N +1; O* -1
C. N +1; O* +1
D. N -1; O* 0
25. Which of the following species have tetrahedral bond angles?
NH3
A
A. A, D and E

CH3
D

CH3+
C

BF3
B
B. A, E

C. A, D, E, F

H2O
E

H3O+
F

H2C=CH2
E

AlCl3
F

D. only D

26. Which of the following species is planar?

CH3+
A

H3O+
C

BF3
B

A. all but C and D

B. A and B

NH4+
D

C. all but C

D. B, E, F

27. In the reaction below, the strongest base is

H2O +NH2 HO+ NH3
B. NH2

A. H2O

C. HO

D. NH3

28. A thorough study of organic chemistry requires a basic understanding of acid and base strengths. Which of the following
molecules most likely has a pKa = 15.5?
A. H2SO4

B. HCl

C. Methanol

D. Methane

E. Acetic Acid

29. Match the hybridization of carbon with the correct electron domain shape
A. sp3
B. sp2
C. sp
A. AX, BY, CZ

B. AZ, BX, CY

X. trigonal
Y. linear
Z. tetrahedral
C. AY, BZ, CX

D. AX, BZ, CY

30. Which is the shortest of the carbon-carbon single bonds indicated by arrows in the following compounds?
CH2

H3C

CH3
A

H3C

C
B

CH

H3C

CH

H2C
HC C

CH

31. For the simple hydrides, MHn, acidities increase in the order:
A. CH4 , NH3 , H2O , H2S , HBr
C. HBr , H2O , NH3 , H2S , CH4
E. H2S , H2O , HBr , NH3 , CH4

B. HBr , H2S , H2O , NH3 , CH4

D. NH3 , H2S , CH4 , H2O , HBr

HC

C CH
E

32. Which acid-base reaction would not take place as written? (Which has an equilibrium constant less than one?)
A.
B.
C.
D.
E.

CH3Li + CH3CH2CH2CH2NH2 CH4 + CH3CH2CH2CH2NHLi

CH3CCH + NaOCH3 CH3CCNa + CH3OH
HCCNa + H2O HCCH + NaOH
CH3OH + NaNH2 CH3ONa + NH3
CH3CO2H + CH3ONa CH3CO2Na + CH3OH

33. Which of the following pairs of bases lists the stronger base first?
A. I- > ClB. H2O > HOC. HO- > H2ND. CH3COO- > HO-

E. H2N- > CH3COO-

34. A group of acids arranged in order of decreasing acidity is:

HNO3 > CH3COOH > C6H5OH > H2O > HCCH
What is the arrangement of the conjugate bases of these compounds in decreasing order of basicity?
A.
B.
C.
D.
E.

NO3 > CH3COO > C6H5O > OH > HCC

CH3COO > C6H5O > NO3 > OH > HCC
C6H5O > NO3 > HCC > OH > CH3COO
HCC > OH > C6H5O > CH3COO > NO3
No prediction of relative base strength is possible.

35. A non-zero dipole moment is exhibited by:

A. BF3

B. CO2

C. CCl4

D. SO2

Cl

Cl

E. Cl

Cl

36. The compound on the right has a formal charge of

A.
B.
C.
D.
E.

-1 on N
+2 on N
-1 on Al
+1 on Br
none of the above

37. The arrow in the structure on the right points to a bond that is formed by
A.
B.
C.
D.

overlap of an s orbital on H and an sp2 orbital on C

overlap of an s orbital on H and an sp orbital on C
overlap of an s orbital on H and an sp3 orbital on C
none of the above

38. Which of the following is a pair of contributing structures?

EXTRA CREDIT
39. Which of the following resonance structures is the most important contributor to the actual molecule?

A.

B.

C.

D.

E.

NAME__________________________________________

DATE___________________

ANSWER SHEET
CHE 275 CHAP 1 ASSIGN
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SS I 2015