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ch03
Student:

1. Identify the conformation of butane shown below.

A. anti
B. gauche
C. skewed
D. eclipsed
2. What is the IUPAC name of the compound shown in the following Newman projection?

A. 1,1,2,2-tetramethylethane
B. 1,2-dimethylethane
C. 2,2,3,3-tetramethylbutane
D. 2,3-dimethylbutane
3. What is the IUPAC name of the compound shown below?

A. 1,2,3-trimethylbutane
B. 2,3-dimethylpentane
C. 2,3,4-trimethylpentane
D. 2-isopropylbutane
4. What is the dihedral (torsion) angle between the two bromine atoms in the following sawhorse drawing?

A. 0o
B. 30o
C. 60o
D. 90o
5. At room temperature, the various conformations of butane
A. do not interconvert; only the anti form is present.
B. do not interconvert, but all conformations are present.
C. interconvert very slowly.
D. interconvert very rapidly.
6. Which statement is correct concerning the relative stabilities of the two conformations, A and B, below?

A. A is more stable.
B. B is more stable.
C. A and B are equal in stabilities.
D. A and B are not equal in stability, but the preferred conformation cannot be determined by inspection.
7. Identify the spatial relationship of the two chlorine atoms.

A. gauche
B. anti
C. eclipsed
D. twist
8. Which statement is correct concerning the relative stabilities of the two conformations, A and B, below?

A. A is more stable.
B. B is more stable.
C. A and B are equal in stabilities.
D. A and B are not equal in stability, but the preferred conformation cannot be determined by inspection.
9. What is the IUPAC name of the following compound?

A. trans-1,4-dimethylcyclohexane
B. cis-1,4-dimethylcyclohexane
C. trans-1,3-dimethylcyclohexane
D. cis-1,3-dimethylcyclohexane
10. What is the dihedral (torsion) angle between the two bromine atoms in the wedge-and-dash drawing
below?

A. 60o
B. 90o
C. 120o
D. 180o
11. Identify the relationship between the following two structures.

A. constitutional isomers
B. stereoisomers
C. different conformations of the same compound
D. identical
12. Predict which of the following constitutional isomers of C5H10 would have the highest heat of
combustion?
A. methylcyclobutane
B. cyclopentane
C. cis-1,2-dimethylcyclopropane
D. trans-1,2-dimethylcyclopropane
13. Identify the two atoms anti to the bromine.

A. the equatorial H's on C-2 and C-6

B. the axial H's on C-2 and C-6
C. C-2 and C-6
D. C-3 and C-5
14. Cyclohexane adopts the chair conformation rather than a planar structure because
I. torsional strain is minimized. II. the C—C—C bond angles are close to 109.5o.
III. there are no 1,3-diaxial interactions in a planar structure.
A. only I
B. only II
C. I and II
D. I, II, and III
15. Identify the relationship between the following two structures.

A. constitutional isomers
B. stereoisomers
C. different conformations of the same compound
D. identical
16. The most stable conformation of the compound shown has

A. all methyl groups equatorial.

B. equatorial methyl groups at C-1 and C-2, axial at C-4.
C. equatorial methyl groups at C-1 and C-4, axial at C-2.
D. equatorial methyl groups at C-2 and C-4, axial at C-1.
17. The most stable chair conformation of cis-1-tert-butyl-3-methylcyclohexane has
A. both groups equatorial.
B. both groups axial.
C. the tert-butyl group equatorial and the methyl group axial.
D. the tert-butyl group axial and the methyl group equatorial.
18. Identify the relationship of the two compounds below.

A. identical
B. constitutional isomers
C. stereoisomers
D. different conformations of the same compound
19.

Identify the correct stereoisomer and the most stable conformation of the following compound.

A. A
B. B
C. C
D. D
20. Identify the relationship of the two compounds below.

A. identical
B. constitutional isomers
C. stereoisomers
D. different conformations of the same compound
21. What is the IUPAC name of the following compound?

A. bicyclo[2.2.2]octane
B. bicyclo[2.2.2]hexane
C. bicyclo[3.3.3]octane
D. bicyclo[3.3.3]hexane
22. Which statement below is true concerning the conversion of cis-1,4-dimethylcyclohexane to trans-1,4-
dimethylcyclohexane?
A. The conversion takes place by chair conformation ring-flipping.
B. You cannot do the conversion without breaking covalent bonds.
C. The conversions takes place by rotating the C(1)─C(2) bond by 180°.
D. The conversion takes place through the skew boat conformations.
23. What is the IUPAC name of the following bicycloalkane?

A. bicyclo[6.3.0]heptane
B. bicyclo[4.1.0]hexane
C. bicyclo[4.2.1]hexane
D. bicyclo[4.1.0]heptane
24. Identify the relationship between the following two structures.

A. identical
B. different conformations of the same compound
C. stereoisomers
D. constitutional isomers
25.

Which isomer of 1-tert-butyl-3-ethyl-5-methylcyclohexane below is thermodynamically the most stable?

A. A
B. B
C. C
D. D
26. What would the C—C—C bond angles be in a planar cyclohexane?
A. 60o
B. 90o
C. 109.5o
D. 120o
27. Identify the relationship between the following two Newman projections.

A. identical
B. stereoisomers
C. different conformations of the same compound
D. constitutional isomers
28. The IUPAC name of the following compound is

A. cis-1,2-dimethylcyclohexane.
B. trans-1,2-dimethylcyclohexane.
C. 1,1-dimethylcyclohexane.
D. cis-1,3-dimethylcyclohexane.
29. The following structure is

A. cis-1,3-dimethylcyclohexane.
B. cis-1,4-dimethylcyclohexane.
C. trans-1,3-dimethylcyclohexane.
D. trans-1,4-dimethylcyclohexane.

30.
The sawhorse drawing of butane below is

A. a gauche conformation.
B. the anti conformation.
C. the least stable eclipsed conformation.
D. the most stable eclipsed conformation.
31. The sawhorse drawing of butane below is the

A. least stable staggered conformation.

B. most stable staggered conformation.
C. least stable eclipsed conformation.
D. most stable eclipsed conformation.
32. Which constitutional isomer of dimethylcyclohexane does not exhibit cis-trans isomerism?
A. 1,1-dimethylcyclohexane
B. 1,2-dimethylcyclohexane
C. 1,3-dimethylcyclohexane
D. 1,4-dimethylcyclohexane
33. What is the estimated dihedral angle between the two methyl groups on the structure shown below?

A. 30o
B. 60o
C. 90o
D. 120o
34. Which one of the following is not a constitutional isomer of trans-1,3-dimethylcyclopentane?
A. 1,1-dimethylcyclopentane
B. cis-1,2-dimethylcyclopentane
C. ethylcyclopentane
D. cis-1,3-dimethylcyclopentane
35.
Which of the following best describes the conformation of propane shown below?

A. C(1) - C(2) staggered and C(2) - C(3) staggered

B. C(1) - C(2) staggered and C(2) - C(3) eclipsed
C. C(1) - C(2) eclipsed and C(2) - C(3) staggered
D. C(1) - C(2) eclipsed and C(2) - C(3) eclipsed
36. Which one of the following is the butane conformation shown below?

A. gauche
B. anti
C. skew
D. eclipsed
37. What is the correct IUPAC name of the following compound?

A. cis-1-ethyl-2-methylcyclohexane
B. trans-1-ethyl-2-methylcyclohexane
C. cis-1-ethyl-6-methylcyclohexane
D. trans-1-ethyl-6-methylcyclohexane
38. Which of the following can have cis-trans stereoisomers?
A. 1,1-dimethylcyclobutane
B. 1,3-dimethylcyclobutane
C. 1,1,3-trimethylcyclobutane
D. 1,1,3,3-tetramethylcylclobutane
39. The C—C—C bond angle in cyclopropane is
A. 60o.
B. 90o.
C. 109.5o.
D. 120o.
40. The most stable conformation of cis-4-methyl-1-tert-butylcyclohexane is a chair conformation with
A. both the -CH3 and -C(CH3)3 equatorial.
B. both the -CH3 and -C(CH3)3 axial.
C. the -CH3 equatorial and the -C(CH3)3 axial.
D. the -CH3 axial and -C(CH3)3 equatorial.
41. What is the IUPAC name of the compound shown below?

A. cis-1,3-dimethylcyclohexane
B. trans-1,3-dimethylcyclohexane
C. cis-1,4-dimethylcyclohexane
D. trans-1,5-dimethylcyclohexane
42. What is the IUPAC name of the compound shown below?

A. cis-1,2-diethylcyclobutane
B. trans-1,2-diethylcyclobutane
C. cis-1,3-diethylcyclobutane
D. trans-1,3-diethylcyclobutane
43. Which is more stable, cis-1,3-dimethylcyclohexane or trans-1,3-dimethylcyclohexane?
A. trans-1,3-dimethylcyclohexane
B. cis-1,3-dimethylcyclohexane
C. They are equally stable.
D. Stabilities of cis, trans stereoisomers cannot be compared.
44. What is the relationship between the following two structures?

A. identical
B. stereoisomers
C. different conformations of the same compound
D. constitutional isomers
 ch03 Key
1. B

2. D

3. B

4. C

5. D

6. C

7. B

8. B

9. A

10. D

11. C

12. C

13. D

14. C

15. B

16. D

17. A

18. C

19. B

20. A

21. A

22. B

23. D

24. C

25. A

26. D

27. C

28. A

29. C

30. A

31. C

32. A

33. B

34. D

35. C

36. A
37. B

38. B

39. A

40. D

41. B

42. C

43. A

44. D
 ch03 Summary
Category # of Questions
Carey - 003 Conformations... 44
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‘The splendid wayfaring’ has compelling force.”

+ Springf’d Republican p10 D 17 ’20 300w

“Mr Neihardt has succeeded in giving some epical quality to his

heroes and painting, as he intended to do, the mood of their
adventures.” M. C. C.

+ − Survey 45:578 Ja 15 ’21 240w

[2]
NEKLIUDOV, ANATOLII VASIL’EVICH.
Diplomatic reminiscences before and during the
world war, 1911–1917; tr. from the French, by
Alexandra Paget. *$8 Dutton

(Eng ed 20–10794)

“A Russian diplomat’s frank statement of what he learned as

Minister to Bulgaria during the Balkan wars of 1912 and of 1913,
supplemented by his observations during the world war, when he
was serving as Minister to Sweden, and Ambassador to Spain.
Writing in the firm conviction that all who took part in the
tremendous events of those years now belong to ‘an irrevocable past,’
M. Nekliudov speaks as freely concerning his contemporaries as if
they were actually dead.”—R of Rs
 “M. Nekliudov, with his tears and his discontents, is not a very
interesting person. The best part of his long book is the record of his
ambassadorship in Sweden during the war, and in his comments on
certain Russian statesmen such as Stürmer and Protopopoff he has
something to say that is not without interest.”

− + Ath p205 Ag 13 ’20 270w

R of Rs 63:109 Ja ’21 90w

“The style is more than clear and studiously temperate: it is at

times eloquent and pathetic, and throughout tinged with the
philosophy natural to a cultured gentleman. The English of
Alexandra Paget is so good that it must, we think, be ranked as a
first-rate translation.”

+ Sat R 130:94 Jl 31 ’20 1000w

+ Spec 124:87 Jl 17 ’20 210w

“Having lost his emperor, his country and his sons, this former
representative of a departed system sees no necessity to guard
certain of those secrets which go to make up the mystery of
diplomacy. In consequence of this break with the past which fate has
forced upon him M. Nekliudov is interesting and informative.”

+ The Times [London] Lit Sup p343 Je 3

’20 1300w

NEW Decameron; second day. *$1.90 McBride

 20–8740

The first volume was published last year. Like it this second
volume is a collection of short stories by different authors, each story
in keeping with the character of its narrator. Contents: Jim of
Moloch’s bar, by Francis Carco: Bread upon the waters, by Michael
Sadleir; The history of Andrew Niggs, by Basil Blackwell; The tool, by
W. F. Harvey; The master-thief, by Dorothy L. Sayers; The affair of
the Mulhaven baby, by M. Nightingale; The vase, by Camilla Doyle;
“Once upon a time” by Bill Nobbs; A prayer perforce, by M. Storm
Jameson; Salvator Street, by Sherard Vines.

“In spite of serious inequalities in the work, the total result is

undoubtedly entertaining. In all the stories there is evidence of
careful workmanship, a preoccupation with literary means which is
highly satisfactory save when it aims at effect with too unchastened
self-consciousness.” F. W. S.

+ Ath p172 Ag 6 ’20 520w

“Some of them are excellent, some rather poor and a few

unequivocally dull. Heralded simply as ‘Salvator street’ comes the
surprise of the book. In it Sherard Vines has succeeded in creating a
character besides writing the best story of the volume.”

+ Boston Transcript p4 D 11 ’20 350w

“The idea of vocational guidance in the telling of tales is not

altogether conducive to the best flights of the imagination. The
obligation to relate the sort of story that a master-printer, a poet, or a
psychic researcher would be apt to relate seems to have put a
restraint upon most of the contributors.” L. B.
 − Freeman 2:501 F 2 ’21 130w

“‘The new Decameron,’ to carry on its excellent plan, must be, like
the ‘Canterbury tales’ which its general method recalls, more
variously human in substance and in modulation. Their
inventiveness in plot and ingenuity in structure are remarkable. But
these are not high qualities in fiction. ‘The new Decameron’ needs
not, indeed, cheerfulness, but sunlight; less smell of the charnel
house and more of the earth.”

− + Nation 111:596 N 24 ’20 260w

“The structure of the book is cleverly contrived, and in reading it

the fact that this is the work of several hands does not obtrude itself
too violently. At its best the book is artistic, and it is always elegant.
The remoteness, the wickedness, and the nervous dread of crudity
dissociate the authors from the literary giants of past times. All the
contributors give an impression of literary taste, and not one of them
has generated a ‘human document.’”

+ − The Times [London] Lit Sup p363 Je 10

’20 550w

[2]
NEWBOLT, SIR HENRY JOHN. Book of
good hunting. il *$3.50 (*10s 6d) Longmans 799

20–18594

“Sir Henry Newbolt has put together many interesting stories

about sport. Elephants, lions, and tigers come first: then there are
chapters on deer-hunting and fox-hunting, with many extracts from
Mr Masefield’s fine poem, ‘Reynard the fox,’ and a closing chapter on
fishing. In his introductory chapter, ‘On the nature of sport,’ he
states the arguments for and against sport, and insists very strongly
on the value of true sportsmanship to the national character.”—Spec

+ Ath p649 N 12 ’20 500w

“Sir Henry Newbolt writes so pleasantly that he will attract readers

of all ages.”

+ Spec 125:710 N 27 ’20 90w

“From a literary or sporting standpoint, the book is equally

attractive.”

+ Springf’d Republican p10 Ja 18 ’21 320w

“The instances of hunting experiences chosen by Sir Henry are

admirably described, and compel the reader to share the excitement
of the hunter. He brings out all the concomitants which differentiate
sport from killing.”

+ The Times [London] Lit Sup p825 D 9

’20 950w
 NEWLAND, H. OSMAN. Romance of modern
commerce. il *$2 Lippincott 380

20–3902

“The book is, as described in its sub-title, a popular account of the

production of a number of common commodities. It collects a mass
of miscellaneous information about wheat and other cereals, tea,
coffee and cocoa, rubber, tobacco, cotton, silk, wool, timber, paper,
fruit and wine, cattle and leather, vegetable and mineral oils, furs
and feathers, precious stones and metals.”—The Times [London] Lit
Sup

“Informative and of varying interest. Could be used by upper

grades and high schools.”

+ Booklist 17:55 N ’20

Brooklyn 12:126 My ’20 20w
R of Rs 62:448 O ’20 30w
+ − The Times [London] Lit Sup p748 D 11
’19 150w

NEWMAN, ERNEST. Musical motley. *$1.50

Lane 780.4

20–1630
 A series of papers by an English musical critic. Among the titles
are: “L’enfant prodigue”; On instruments and their players; On
musical surgery; Criticism by code; Futurist music; The best hundred
scores.

“Mr Newman is a musician of the nineteenth century. This must

not be taken to mean that he is an old-fashioned pedant who is out of
touch with new developments. On the contrary, he is intensely
interested in modern music and has no sentimental illusions about
that of the past. Music is for him always a thing of the living present.”
E: J. Dent

+ Ath p1010 O 10 ’19 900w

+ Booklist 16:232 Ap ’20

“Mr Newman is never dull, even when he is grave.” H: T. Finck

+ Bookm 51:169 Ap ’20 440w

“The chief attraction of Mr Newman’s book, besides its dry humor,

is its lack of dogmatism and its corresponding illumination of
speculative points.” M. H.

+ New Repub 22:168 Mr 31 ’20 520w

+ R of Rs 61:224 F ’20 80w

“He differs from a good many fashionable critics in his familiarity

with the works of the ancients, and in testing the moderns by
standards which these critics are either ignorant of, or refuse to
accept. Perhaps the wisest and sanest passages in the book are those