ch015

Chapter 15 Organic Compounds and the Atomic Properties of Carbon

Student: ______________________________________________________________________

1. Select the correct name for this compound.

A. 1,1,3-triethyl-2-methylbutaneB. 1,1-diethyl-2,3-dimethylpentaneC. 2,4-diethyl-3-methylhexaneD. 3-ethyl-4,5-dimethylheptaneE. None of these choices is correct.


A. 2-isopropyl-2,3,4-trimethylbutaneB. 2-isopropyl-2,3-dimethylpentaneC. 2,3,3,4-tetramethylhexaneD. 1,1,2,2,3-pentamethylpentaneE. None of these choices is correct.


A. 1,2-diethyl-1-methyl-3-propyl-4-isobutylhexaneB. 1,6,6-trimethyl-1,2,4-triethyl-3-propylhexaneC. 1,1,6-trimethyl-3,5,6-triethyl-4-propylhexaneD. 4,6-diethyl-2,7-dimethyl-5-propylnonaneE. 3,5-diethyl-1,1,6-trimethyl-4-propyloctane


A. 2,4,5-tripropylheptaneB. 6-methyl-3,4-dipropylnonaneC. 4-ethyl-5,7-dipropyloctaneD. 5-ethyl-2,4-dipropyloctaneE. 4-ethyl-7-methyl-5-propyldecane

5. Select the correct name for the following compound.

A. ortho-dipropylcyclopentylhexaneB. 2,3-dipropylcyclopentylhexaneC. 2-hexyl-1,5-dipropylcyclopentaneD. 1-hexyl-2,3-dipropylcyclopentaneE. 1,2-dipropyl-3-hexylcyclopentane


A. ortho-ethylheptylcyclopentaneB. meta-ethylheptylcyclopentaneC. 1-ethyl-2-heptylcyclopentaneD. ethylcyclopentylheptaneE. ortho-ethylheptylbenzene


A. 1-ethyl-3-methylcyclohexaneB. 1-methyl-5-ethylcyclohexaneC. meta-ethylmethylcyclohexaneD. meta-ethylmethylbenzeneE. 3-ethyltoluene


A. cis-2-methyl-4-hepteneB. trans-2-methyl-4-hepteneC. cis-6-methyl-3-hepteneD. trans-6-methyl-3-hepteneE. cis-2-methyl-3-heptene


A. cis-3-ethyl-2,6-dimethyl-6-propyl-4-noneneB. trans-3-ethyl-2,6-dimethyl-6-propyl-4-noneneC. cis-7-ethyl-4,8-dimethyl-4-propyl-5-noneneD. trans-7-ethyl-4,8-dimethyl-4-propyl-5-noneneE. None of these choices is correct.


A. cis-2-methyl-2,3-dipropyl-4-octeneB. cis-7-methyl-6,7-dipropyl-4-octeneC. cis-4,4-dimethyl-5-propyl-6-deceneD. trans-7,7-dimethyl-6-propyl-4-deceneE. cis-7,7-dimethyl-6-propyl-4-decene


A. cis-2,3-dimethyl-4-hexeneB. trans-2,3-dimethyl-4-hexeneC. cis-4,5-dimethyl-2-hexeneD. trans-4,5-dimethyl-2-hexeneE. trans-4,5-dimethyl-2-heptene


A. cis-2,5-diethyl-6-methyl-3-noneneB. 2,5-diethyl-6-methyl-3-noneneC. cis-4,6-diethyl-3-methyl-6-noneneD. 4,6-diethyl-3-methyl-6-noneneE. trans-2,5-diethyl-6-methyl-3-nonene


A. 2-ethyl-3-penteneB. 4-ethyl-2-penteneC. 3-methyl-4-hexeneD. 4-methyl-2-hexeneE. None of these choices is correct.


A. 1,1-diethyl-3-butyl-3-hexeneB. 5-butyl-3-ethyl-5-octeneC. 4-butyl-6-ethyl-3-octeneD. 3-ethyl-5-propyl-5-noneneE. 4-butyl-6-ethyl-3,4-octene


A. 1-butyl-4-pentyl-3-propylcyclohexeneB. 1-butyl-4-pentyl-5-propylcyclohexeneC. 2-butyl-5-pentyl-6-propylcyclohexeneD. 4-butyl-1-pentyl-2-propylcyclohexeneE. 1-butyl-4-pentyl-3-propylbenzene


A. 1,1-dimethyl-1-cylcopentyl-2-pentaneB. 1,1-dimethyl-2-hexene-cyclopentaneC. 2-cyclopentyl-2-methyl-3-hexeneD. 5,5-dimethyl-5-cyclopentyl-3-pentaneE. 5,5-dimethyl-5-cyclopentyl-3-pentene


A. 2-ethyl-4-propylcyclohepteneB. 3-ethyl-5-propylcyclohepteneC. 6-ethyl-4-propylcyclohepteneD. 7-ethyl-5-propylcyclohepteneE. 3-ethyl-5-propylcyclohexene


A. 4-ethyl-1,1,5-trimethyl-2-heptyneB. 4,5-diethyl-1,1-dimethyl-2-heptyneC. 5-ethyl-2,6-dimethyl-3-octeneD. 3-ethyl-3,7-dimethyl-5-octyneE. 5-ethyl-2,6-dimethyl-3-octyne


A. 5-butyl-4,4-dimethyl-3-propyl-1-hepteneB. 5-ethyl-4-4-dimethyl-3-propyl-1-nonyneC. 5-ethyl-6-6-dimethyl-7-propyl-8-nonyneD. 4,6-diethyl-5-5-dimethyl-4-decyneE. 5-ethyl-4-4-dimethyl-3-propyl-1-nonene


A. 4-4-diethyl-2-pentyneB. 2,2-diethyl-3-pentyneC. 2-ethyl-2-methyl-4-hexyneD. 4-ethyl-4-methyl-2-hexyneE. 2-ethyl-2-methyl-4-hexene


A. 2,5-dimethyl-3-octyne-6-cyclobutaneB. 4-cyclobutyl-1-isopropyl-3-methyl-1-hexyneC. 3-cyclobutyl-4,7-dimethyl-5-octyneD. 6-cyclobutyl-2,5-dimethyl-3-octyneE. 3-cyclobutyl-4,7-dimethyl-5-octene


A. meta-chloroethylcyclohexeneB. 1-chloro-5-ethylcyclohexeneC. meta-chloroethylbenzeneD. 1-chloro-5-ethylbenzeneE. 1-chloro-3-ethylcyclohexane


A. 1-chloro-2-ethyl-3-propylcyclohexaneB. 1-chloro-2-ethyl-3-propylcyclohexeneC. 1-chloro-ortho-ethylpropylbenzeneD. 1-chloro-meta-ethylpropylbenzeneE. 1-chloro-2-ethyl-3-propylbenzene


A. ortho-butylethylbenzeneB. meta-butylethylbenzeneC. para-butylethylbenzeneD. 1-butyl-2-ethylcyclohexeneE. 1-butyl-2-ethylcyclohexane


A. ortho-dibromobenzeneB. meta-dibromobenzeneC. para-dibromobenzeneD. 1,4-dibromocyclohexeneE. 1,4-dibromocyclohexane


A. para-bromochloro-2-ethylbenzeneB. 4-bromo-1-chloro-2-ethylbenzeneC. 5-bromo-2-chloro-1-ethylbenzeneD. 1-bromo-4-chloro-3-ethylcyclohexeneE. 4-bromo-1-chloro-2-ethylcyclohexane


A. 3,4-diethyl-4-methyl-2-butanolB. 2,3-diethyl-4-pentanolC. 3,4-diethyl-2-pentanolD. 3-ethyl-4-methyl-2-hexanolE. 3-ethyl-4-methyl-2-hexanal

28. What is the molecular formula of the compound 2,3-dimethyl-4-cyclopentyl-5-ethyldecane? A. C16H34

B. C17H34

C. C18H36

D. C19H38

E. C20H40

29. What is the difference between 1-butyne and 1-butene? A. 1 carbon atomB. 1 carbon atom and 2 hydrogen atomsC. 2 hydrogen atomsD. 4 hydrogen atomsE. 1 carbon atom and 4 hydrogen atoms


A. 3-ethyl-2,3-dimethyl-1-propanolB. 2,3,4-trimethyl-1-butanolC. 2,3-dimethyl-1-pentanolD. 3,4-dimethyl-5-pentanolE. 2,3-dimethyl-1-pentanal

31. Which compound, if any, will be optically active?

A.

B.

C.

D.E. None of these choices is optically active.

32. Which compound, if any, will not be optically active?

A.

B.

C.

D.E. They are all optically active.

33. Excluding cyclic compounds, how many possible isomers exist for C4H8? A. 2B. 4C. 5D. 6E. 7

34. Including cyclic compounds, how many possible isomers exist for C4H8? A. 2B. 4C. 5D. 6E. 7

35. Which of the following features do cyclohexene and 3-methyl-1-pentyne have in common? A. same physical propertiesB. same chemical propertiesC. same boiling pointD. same molecular weightE. same number of double bonds

36. Select the correct type for the following reaction.CH3CH2CH2CH2OH + HBr CH3CH2CH2CH2Br + H2O A. dehydrationB. dehydroxylationC. additionD. eliminationE. substitution

37. Alcohols undergo a variety of reactions. Which one of the following reactions is not undergone by the alcohol functional group? A. substitutionB. additionC. dehydrationD. oxidation to form a ketoneE. oxidation to form an aldehyde or a carboxylic acid

38. Benzene will react with chloromethane in the presence of a catalyst to produce toluene and hydrogen chloride. Select the correct reaction type for the process.

A. additionB. eliminationC. substitutionD. oxidationE. reduction

39. Select the correct reaction type for the following process.


40. The reaction of bromine with an alkene such as cyclopentene is a good laboratory test for the presence of a double bond in a compound. What type of reaction is it?

A. additionB. eliminationC. substitutionD. displacementE. reduction

41. 2-chloro-2,3-dimethylbutane will react with potassium hydroxide dissolved in alcohol to produce 2,3-dimethyl-2-butene. What type of reaction is this?

A. additionB. eliminationC. substitutionD. oxidationE. displacement

42. Select the correct type for the following reaction.

A. additionB. eliminationC. substitutionD. oxidationE. dehydrogenation


A. additionB. eliminationC. carbonylationD. dehydrationE. oxidation



45. Identify the functional group circled.

A. aldehydeB. ketoneC. alcoholD. esterE. carboxylic acid

46. Vanillin is a flavoring agent which occurs naturally in the vanilla bean, the seed of an orchid. Identify the functional group circled.

A. aldehydeB. ketoneC. alcoholD. carboxylic acidE. carbonyl

47. One source of a musky odor in perfumes is civetone, a compound extracted from the scent gland of the civet cat. Identify the functional group circled.

A. aldehydeB. ketoneC. alcoholD. carboxylic acidE. oxide

48. Aspirin is an effective and widely used pain reliever. Identify the functional group circled.

A. aldehydeB. ketoneC. esterD. carboxylic acidE. carbonyl

49. Enflurane is an effective gaseous anesthetic with relatively low flammability. Identify the functional group circled.

A. aldehydeB. ketoneC. esterD. etherE. alcohol

50. Anethole, a derivative of anise, is used in flavoring and as perfume in soap and toothpaste. Identify the functional group circled.

A. aldehydeB. ketoneC. alcoholD. esterE. ether

51. Glycerin is used in cosmetics as a moisturizer. Identify the functional group circled.

A. carboxylic acidB. alcoholC. esterD. etherE. aldehyde

52. Glucose is an important sugar in a person's metabolic cycle. Identify the functional group circled.

A. aldehydeB. ketoneC. alcoholD. esterE. carboxylic acid

53. Testosterone is a male hormone. Identify the functional group circled.

A. aldehydeB. ketoneC. alcoholD. esterE. carboxyl

54. The compound shown below is responsible for the odor in rancid butter. Identify the functional group circled.

A. aldehydeB. ketoneC. alcoholD. carboxylic acidE. carbonyl

55. Benzocaine is from a family of chemicals that are good local anesthetics. Identify the functional group circled.

A. aldehydeB. ketoneC. esterD. carboxylic acidE. carbonyl

56. Putrescine is produced during the decay and protein breakdown of meats and is responsible for some of the odor found in them. Identify the functional group circled.

A. aldehydeB. ketoneC. amideD. nitrileE. amine

57. Serotonin transmits nerve impulses through the body. Identify the functional group circled.

A. aldehydeB. alcoholC. amideD. amineE. nitride

58. Acetominophen is a widely used and an effective pain reliever. Identify the functional group circled.

A. aldehydeB. alcoholC. amideD. amineE. carbonyl

59. Urea carries waste nitrogen from the body in urine. Identify the functional group circled.

A. aldehydeB. alcoholC. carboxylD. amineE. amide

60. The millipede ejects the compound shown below to protect itself from its enemies. Identify the functional group circled.

A. nitrileB. alcoholC. amideD. amineE. nitro

61. Amygdalin (Laetrile) was once touted for its potential anticancer activity. However, the claims were never scientifically verified. Identify the functional group circled.

A. carboniteB. etherC. amideD. amineE. nitrile

62. Which one of the following classes of organic compound does not contain the carbonyl (C O) group? A. aldehydesB. carboxylic acidsC. ketonesD. alcoholsE. esters

63. Identify the principal organic product of the reaction between butane and chlorine.

A. CH3ClB. CH3CH2ClC. CH3CHClCH3

D. CH3CH2CHClCH3

E. None of these choices is a major product of the reaction.

64. Identify the principal organic product when benzyl chloride reacts with aqueous sodium hydroxide.

A.

B.

C.

D.E. None of these choices is correct.

65. Identify the two principal products of the reaction between ammonia and ethyl propionate.

A.

B.

C.

D.E. None of these choices is correct.

66. Identify the products of the following reaction.

A.

B.

C.

D.E. None of the above pairs of compounds is formed in the reaction.

67. Identify the products for the reaction between cycloheptene and bromine.

A.

B.

C.

D.E. None of these choices is among the products of the reaction.

68. Identify the products of the reaction of 3-octene with chlorine.

A.

B.

C.

D.

E.

69. Identify the products of the reaction between 2-bromopentane and potassium ethoxide.

A.

B.

C.

D.E. None of these choices is among the products of the reaction.

70. Identify the principal organic products for the following reaction.

A.

B.

C.

D.E. None of these choices is among the principal organic products of the reaction.

71. Identify the organic product when cyclohexanol reacts with excess potassium dichromate in the presence of sulfuric acid.

A.

B.

C.

D.E. None of these choices is the organic product of the reaction.

72. Identify the organic product when 3-cylcobutyl-1-propanol reacts with excess potassium dichromate in sulfuric acid.

A.

B.

C.


73. Identify the organic product for the reaction of 2-pentanol with sulfuric acid.

A.

B.

C.


74. Identify the organic product when cyclopentanol reacts with sulfuric acid.

A.

B.

C.


75. One characteristic of the monomers that form condensation polymers that is not common in monomers which form addition polymers is A. the presence of pi bonds.B. the presence of two functional groups.C. the presence of alkyl side chains.D. the ability to form free radicals.E. the presence of sulfur atoms.

76. Which of the following polymers is a condensation polymer? A. polystyreneB. TeflonC. polyvinylchlorideD. polypropyleneE. Dacron

77. Nylon-type compounds are prepared by the reaction of A. a diol with a diacid.B. an alcohol with a diacid.C. a diamine with a diacid.D. an amine with a diacid.E. a diamine with an acid.

78. Dacron is a ___________ compound and is produced by a __________ reaction. A. polyamide; additionB. polyamide; condensationC. polyester; additionD. polyester; condensationE. polyene; addition

79. The most abundant organic chemical on earth is A. glycogen.B. starch.C. cellulose.D. glucose.E. carbonate.

80. Each amino acid has two functional groups in common and one of 20 other groups attached to the -carbon. The two functional groups are A. carboxyl and amine.B. ester and amine.C. carboxyl and amide.D. alcohol and amine.E. carboxyl and peptide.

81. Helical and sheet-like segments in proteins arise from A. disulfide bridges.B. salt bridges.C. crosslinking via covalent bonds.D. dispersion forces within the protein's interior.E. hydrogen bonding.

82. The protein amino acid sequence, the RNA base sequence, and the DNA base sequence are interrelated. Which of the following descriptions is correct? A. The RNA base sequence determines the DNA base sequence which, in turn,

determines the protein amino acid sequence.B. The DNA base sequence determines the RNA base sequence which, in turn,

determines the protein amino acid sequence.C. The DNA base sequence determines the protein amino acid sequence which, in turn,

determines the RNA base sequence.D. The RNA base sequence determines the protein amino acid sequence which, in turn,

determines the DNA base sequence.E. None of these choices is correct.

83. Draw and name two non-alkenes with the formula C4H8.

84. Draw and name all stable molecules with the formula C5H12.

85. Draw and name four alkenes with the formula C4H8.

86. Name the compound with the molecular structure shown.

87. Draw the structure of trans-5-methyl-3-heptene.

88. Name these compounds:

89. What is the simplest molecular formula fora. an alkane capable of having structural isomers?b. an alkane capable of having optical isomers?c. an alkene capable of having geometrical isomers?

90. In one sentence, what is the general requirement for a molecule to be optically active?

91. a. Draw two different structures with the molecular formula C2H6O.b. Name the functional group in each structure.c. Which one will have the higher boiling point, and why?

92. Name each of the following functional groups:

93. Write down the structure of the missing organic reactant or product(s) in the following reactions, and name the type of reaction involved (inorganic products may also be formed):

94. Describe and contrast fibrous and globular proteins in terms of their amino acid composition, their structure and their function.

95. Explain how a disulfide bridge can arise a protein molecule.

96. Explain how a salt bridge can arise a protein molecule.

97. Name the three component parts of a nucleotide.

98. Explain what is meant by "complementary" in the context of DNA strands.

99. Given that each 3-base sequence in DNA is a "code word" for a particular amino acid, how many different code words are possible using a 3-base sequence and the bases available in DNA?

100. Because organic compounds are associated with living organisms, their properties are governed by fundamentally different chemical principles from those of inorganic compounds. Difficulty: E True False

101. Ethane (C2H6) is much more reactive than disilane (Si2H6). Difficulty: E True False

102. The carbon atoms in a molecule of cyclohexane lie in the same plane. Difficulty: M True False

103. All the atoms in a molecule of benzene lie in the same plane. Difficulty: M True False

104. Both alkenes and alkynes exhibit geometric (cis/trans) isomerism. Difficulty: E True False

105. Because of delocalization, all the carbon-carbon bond lengths in 1,3-cyclopentadiene are identical. Difficulty: E True False

106. As a result of delocalization of the pi-electrons, all the carbon-carbon bonds in benzene are identical. Difficulty: E True False

107. A characteristic reaction of alkanes is addition. Difficulty: E True False

108. A characteristic reaction of alkenes is addition. Difficulty: E True False

109. A characteristic reaction of haloalkanes is substitution. Difficulty: E True False

110. All alcohols are capable of hydrogen bonding. Difficulty: M True False

111. All ketone molecules are capable of hydrogen bonding to other ketone molecules. Difficulty: M True False

112. Carboxylic acids are weak acids. Difficulty: M True False

113. Secondary amines have the general formula RNH2. Difficulty: E True False

114. Esters can be formed by the dehydration-condensation of a carboxylic acid and an alcohol. Difficulty: M True False

115. Addition polymers are mostly made from monomers with carbon-carbon double bonds. Difficulty: M True False

116. Condensation polymers are formed by free radical addition reactions. Difficulty: M True False

117. Both nylons and proteins are polyamides. Difficulty: M True False

118. Amino acids in solution can undergo an internal acid-base reaction. Difficulty: M True False

119. The backbone of protein molecules consists of repeating N C C O units. Difficulty: M True False

Chapter 15 Organic Compounds and the Atomic Properties of Carbon Key1. (p. 636) D 2. (p. 636) C 3. (p. 636) D 4. (p. 636) E 5. (p. 643) D 6. (p. 643) C 7. (p. 643) A 8. (p. 643) C 9. (p. 643) B 10. (p. 643) E 11. (p. 643) D 12. (p. 643) B 13. (p. 643) D 14. (p. 643) C 15. (p. 643) A 16. (p. 643) C 17. (p. 643) B 18. (p. 643) E 19. (p. 643) B 20. (p. 643) D 21. (p. 643) D 22. (p. 652) C 23. (p. 652) E 24. (p. 644) A 25. (p. 652) C 26. (p. 652) B 27. (p. 651) D 28. (Sec. 15.2) D

29. (Sec. 15.2) C 30. (p. 651) C 31. (p. 639) B 32. (p. 639) D 33. (Sec. 15.2) B 34. (Sec. 15.2) D 35. (Sec. 15.2) D 36. (Sec. 15.3) E 37. (Sec. 15.4) B 38. (Sec. 15.3) C 39. (Sec. 15.3) A 40. (Sec. 15.3) A 41. (Sec. 15.3) B 42. (Sec. 15.3) B 43. (Sec. 15.3) E 44. (Sec. 15.3) D 45. (p. 651) E 46. (p. 651) D 47. (p. 651) B 48. (p. 651) C 49. (p. 651) D 50. (p. 651) E 51. (p. 651) B 52. (p. 651) A 53. (p. 651) B 54. (p. 651) D 55. (p. 651) C 56. (p. 651) E 57. (p. 651) D 58. (p. 651) C 59. (p. 651) E

60. (p. 651) A 61. (p. 651) E 62. (p. 651) D 63. (Sec. 15.4) D 64. (p. 654) A 65. (p. 659) B 66. (p. 658) B 67. (p. 649) B 68. (p. 649) A 69. (p. 652) C 70. (p. 652) B 71. (p. 652) B 72. (p. 652) C 73. (p. 650) D 74. (p. 650) B 75. (p. 664) B 76. (p. 665) E 77. (p. 664) C 78. (p. 665) D 79. (p. 666) C 80. (p. 667) A 81. (p. 669) E 82. (p. 672) B

83. (p. 643) Difficulty: E

84. (p. 643)

Difficulty: M

85. (p. 643) Difficulty: M

86. (p. 643) 2-methyl-2-pentene

Difficulty: M

87. Difficulty: M

88. (p. 643) a. cyclobutane

b. cyclooctenec. toluene (methylbenzene)Difficulty: E

89. (p. 643) a. C4H10

b. C7H16

c. C4H8

Difficulty: H 90. (p. 639) In order to be optically active, the compound must have a non-superimposable mirror image.

Difficulty: M 91. (p. 651) a. H3C—CH2—OH and H3C—O—CH3

b. alcohol and etherc. The alcohol will have the higher boiling point; it will have hydrogen bonding while the ether does not.Difficulty: M

92. (p. 651) a. alcohol

b. etherc. ketoned. aldehydee. carboxylic acidf. amideDifficulty: E

93. (Sec. 15.4) A.

B.

C.

D.

E.

F.

G.

H. Difficulty: M

94. (p. 669) Fibrous proteins are composed of relatively few amino acids in a repeating pattern. Their structures are helices or

sheets, and they are found in hair, skin and muscle. Globular proteins use more amino acids in their structures, and they have various of irregular shapes. Their functions are various: messenger molecules, enzymes (catalysts), etc.Difficulty: M

95. (Sec. 15.6) Disulfide bridges arise when two cysteine S H side chains react to form a covalent S

S link between the two regions of the protein backbone. The two regions of the protein backbone are thus held together.Difficulty: H

96. (Sec. 15.6) A salt bridge is the result of ionic attraction between a side chain with a carboxylate ( COO¯) group and

one with a protonated amine group ( NH3+). These regions of the molecule are then held together by this ionic

attraction.Difficulty: H

97. (p. 670) phosphate, base, sugar

Difficulty: E

98. (p. 671) Each nucleotide along a single strand of DNA has one of four possible bases, namely guanine (G), cytosine (C), adenine (A) and thymine (T). The double helix of DNA is held in place by hydrogen bonds between pairs of bases, one base being on each of the two strands. G always pairs with C and A always pairs with T. Thus, the base sequence on one strand determines the base sequence on the other strand, and the strands are "complementary" to each other.Difficulty: M

99. (p. 671) 4 4 4 = 64

Difficulty: M 100. (p. 629) FALSE 101. (p. 630) FALSE 102. (p. 644) FALSE 103. (p. 644) TRUE 104. (p. 641) FALSE 105. (Sec. 15.2) FALSE 106. (p. 644) TRUE 107. (p. 647) FALSE 108. (p. 655) TRUE 109. (p. 652) TRUE 110. (p. 650) TRUE 111. (p. 656) FALSE 112. (p. 658) TRUE 113. (p. 653) FALSE 114. (p. 659) TRUE 115. (p. 663) TRUE 116. (p. 664) FALSE 117. (Sec. 15.5, 15.6) TRUE 118. (p. 668) TRUE 119. (p. 668) FALSE

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