QOI 0809 alkynes Name___________________________________ ESSAY. Write your answer in the space provided or on a separate sheet of paper. 1) Give the IUPAC name for (CH 3 ) 2 C(CH 2 CH 3 )CCCH(CH 3 ) 2 . 2) Give the IUPAC name for HCCCH 2 CH 2 CH 3 . 3) Give the IUPAC name for CH 3 CH 2 CCCH(OH)CH 3 . 4) Give the IUPAC name for CH 3 CHCHCHCHCCCH 3 . 5) Give the IUPAC name for BrCH 2 CH 2 CCCH 2 CH 3 . 6) Draw an acceptable structure for acetylene. 7) Draw an acceptable structure for 3-sec -butylhept-1-yne. 8) Draw an acceptable structure for ( S)-5-phenyloct-2-yne. 9) Draw an acceptable structure for hepta -3,6-dien-1-yne. 10) Draw an acceptable structure for hex- 2-yne. MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 11) How many distinct terminal alkynes exist with a molecular formula of C 5 H 8 ? A) 1 B) 2 C) 3 D) 4 E) 5 11) 12) How many distinct internal alkynes exist with a molecular formula of C 6 H 10 ? A) 1 B) 2 C) 3 D) 4 E) 5 12) 13) The carbon-carbon triple bond of an alkyne is composed of __________. A) three σ bonds B) one σ bond and two π bonds C) two σ bonds and one π bond D) three π bonds 13) 14) In trans -hept-4-en-2-yne the shortest carbon-carbon bond is between carbons __________. A) 1 and 2 B) 2 and 3 C) 3 and 4 D) 4 and 5 E) 6 and 7 14) 15) Which of the following improperly describes the physical properties of an alkyne? A) insoluble in most organic solvents B) nearly insoluble in water C) boiling point nearly the same as an alkane with similar carbon skeleton D) less dense than water E) relatively nonpolar 15) 1
Transcript
QOI 0809 alkynes
Name___________________________________
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
1) Give the IUPAC name for (CH3)2C(CH2CH3)CCCH(CH3)2.
2) Give the IUPAC name for HCCCH2CH2CH3.
3) Give the IUPAC name for CH3CH2CCCH(OH)CH3.
4) Give the IUPAC name for CH3CHCHCHCHCCCH3.
5) Give the IUPAC name for BrCH2CH2CCCH2CH3.
6) Draw an acceptable structure for acetylene.
7) Draw an acceptable structure for 3-sec-butylhept-1-yne.
8) Draw an acceptable structure for (S)-5-phenyloct-2-yne.
9) Draw an acceptable structure for hepta-3,6-dien-1-yne.
10) Draw an acceptable structure for hex- 2-yne.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
11) How many distinct terminal alkynes exist with a molecular formula of C5H8?
A) 1 B) 2 C) 3 D) 4 E) 5
11)
12) How many distinct internal alkynes exist with a molecular formula of C6H10?
A) 1 B) 2 C) 3 D) 4 E) 5
12)
13) The carbon-carbon triple bond of an alkyne is composed of __________.
A) three σ bonds B) one σ bond and two π bonds
C) two σ bonds and one π bond D) three π bonds
13)
14) In trans-hept-4-en-2-yne the shortest carbon-carbon bond is between carbons __________.
A) 1 and 2 B) 2 and 3 C) 3 and 4 D) 4 and 5 E) 6 and 7
14)
15) Which of the following improperly describes the physical properties of an alkyne?
A) insoluble in most organic solvents
B) nearly insoluble in water
C) boiling point nearly the same as an alkane with similar carbon skeleton
D) less dense than water
E) relatively nonpolar
15)
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ESSAY. Write your answer in the space provided or on a separate sheet of paper.
16) How many moles of water are produced when one mole of propyne undergoes complete combustion?
17) Why are terminal alkynes more acidic then other hydrocarbons?
18) Provide the structure of the major organic product(s) in the reaction below.
19) Provide the structure of the major organic product(s) in the reaction sequence below.
CH3CH2CCH 1. NaNH2
2. PhCH2Br→
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
20) Which of the species below is less basic than acetylide?
A) CH3ONa
B) CH3Li
C) CH3MgBr
D) both A and C
E) all of the above
20)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
21) Describe a qualitative, nonspectroscopic means for distinguishing terminal alkynes from internal ones.
22) 2-Methylhex-3-yne can be prepared by the reaction of an alkynide with an alkyl halide. Does the better
synthesis involve alkynide attack on bromoethane or on 2-bromopropane? Explain your reasoning.
23) Provide the structure of the major organic product(s) in the reaction below.
24) Provide the structure of the major organic product(s) in the reaction below.
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25) Provide the structure of the major organic product(s) in the reaction sequence below.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
26) When 2,2-dibromobutane is heated at 200°C in the presence of molten KOH, what is the major
organic product?
A) but-1-yne
B) 1-bromobut-2-yne
C) 1-bromobut-1-yne
D) but-1-ene
E) but-2-yne
26)
27) A mixture of hept-1-yne, hept-2-yne, and hept-3-yne was hydrogenated in the presence of a
platinum catalyst until hydrogen uptake ceased. If one assumes that the hydrogenation went to
completion, how many different seven-carbon hydrocarbons were produced?
A) 2 B) 1 C) 3 D) 8 E) 6
27)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
28) Provide the structure of the major organic product(s) in the reaction below.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
29) In the reduction of alkynes using sodium in liquid ammonia, which of the species below is not
thought to be an intermediate in the commonly accepted mechanism?
A) vinyl radical B) vinyl anion C) vinyl cation D) radical anion
29)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
30) Provide the structure of the major organic product(s) in the reaction below.
31) Provide the structure of the major organic product(s) in the reaction below.
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MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
32) In the addition of hydrogen bromide to alkynes in the absence of peroxides, which of the following
species is thought to be an intermediate?
A) vinyl radical
B) vinyl anion
C) vinyl cation
D) carbene
E) none of the above
32)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
33) Provide the structure of the major organic product(s) in the reaction below.
34) Provide the structure of the major organic product(s) in the reaction sequence below.
35) Treatment of hex-2-yne with mercuric sulfate in dilute sulfuric acid yields a mixture of two ketones. Similar
treatment of hex-3-yne produces a single ketone instead of a mixture. Explain.
36) Provide the structure of the major organic product(s) in the reaction below.
37) Provide the structure of the major organic product(s) in the reaction below.
CH3CH2CH2CH2CH2CCCH2CH3 1. O3
2. H2O→
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
38) Among the compounds water, but-1-yne, but-2-yne, and ethane, which are stronger acids than
ammonia?
A) water and but-1-yne B) water and ethane
C) but-1-yne and but-2-yne D) but-1-yne and ethane
38)
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39) To a solution of propyne in diethyl ether, one molar equivalent of CH3Li was added and the
resulting mixture was stirred for 0.5 hour. After this time, an excess of D2O was added. Describe
the major organic product(s) of this reaction.
A) CH3CCD + CH4
B) CH3CCCD3
C) CH3CCCH3
D) CD3CCD3
E) CH3CCD + CH3D
39)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
40) Provide the structure of the major organic product(s) in the reaction below.
PhCCPh D2
Pd/BaSO4, quinoline→
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
41) __________ is produced when 1 equivalent of HBr is added to hex-1-yne in the presence of
peroxides.
A) Z-1-Bromohex-1-ene
B) E-2-Bromohex-2-ene
C) A mixture of E and Z isomers of 1-bromohex-1-ene
D) E-1-Bromohex-1-ene
E) 2-Bromohex-1-ene
41)
42) Which of the alkyne addition reactions below involve(s) an enol intermediate?
A) hydroboration/oxidation
B) treatment with HgSO4 in dilute H2SO4
C) hydrogenation
D) both A and B
E) none of the above
42)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
43) Draw the products which result when oct-3-yne is heated in basic potassium permanganate solution.
44) Describe a sequence of reactions by which racemic 2,3-dibromobutane can be straightforwardly prepared from
propyne.
45) Describe a sequence of reactions by which hexan-2-ol can be straightforwardly prepared from hex-1-yne.
46) Describe a sequence of reactions by which hept-3-yne can be straightforwardly prepared from acetylene.
47) Describe a sequence of reactions by which meso-2,3-dibromobutane can be straightforwardly prepared from
propyne.
48) Describe a sequence of reactions by which hept-1-yne can be straightforwardly prepared from hept-1-ene.
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49) Describe a sequence of reactions by which butylbenzene can be straightforwardly prepared from
phenylacetylene.
50) Describe a sequence of reactions by which (E)-5-bromopent-2-ene can be straightforwardly prepared from
propyne.
51) Describe a sequence of reactions by which CH3CH2CH2COCH2CH3 can be straightforwardly prepared from
but-1-yne.
52) Describe a sequence of reactions by which trans-pent-2-ene can be straightforwardly prepared from propyne.
53) Describe a sequence of reactions by which meso-hexane-3,4-diol can be straightforwardly prepared from
hex-3-yne.
54) Describe a sequence of reactions by which (Z)-hex-3-en-1-ol can be straightforwardly prepared from
but-1-yne.
55) Describe a sequence of reactions by which 1-propylcyclohexan-1-ol can be straightforwardly prepared from
propyne.
56) Describe a sequence of reactions by which the compound shown below can be straightforwardly prepared from
acetylene.
57) Describe a sequence of reactions by which the compound shown below can be straightforwardly prepared from
acetylene.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
58) How many moles of oxygen are required in the complete combustion of 1 mole of acetylene?
A) 1.5 B) 2 C) 3 D) 2.5 E) 1
58)
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
59) Give the IUPAC name for Cl3CCH2CH2CH2C≡CH. 59)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
60) How many distinct alkynes exist with a molecular formula of C4H6?
A) 0 B) 1 C) 2 D) 3 E) 4
60)
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61) How many distinct alkynes exist with a molecular formula of C4H8?
A) 0 B) 1 C) 2 D) 3 E) 4
61)
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
62) Name the compound which results when pent-2-yne is subjected to catalytic
hydrogenation using a platinum catalyst.
62)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
63) Which of the following reagents should be used to convert hex-3-yne to (E)-hex-3-ene?
A) HgSO4, H2O
B) H2, Pt
C) H2, Lindlar's catalyst
D) H2SO4, H2O
E) Na, NH3
63)
64) Which of the following reagents should be used to convert hex-3-yne to (Z)-hex-3-ene?
A) HgSO4, H2O
B) H2, Lindlar's catalyst
C) H2SO4, H2O
D) Na, NH3
E) H2, Pt
64)
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
65) Name the product which results when CH3CCLi reacts with CH3CH2COCH2CH3
followed by addition of water.
65)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
66) Which of the following reagents should be used to convert an internal alkyne to an α-diketone?
A) KMnO4, H2O, neutral
B) Na, NH3
C) O3 then H2O
D) HgSO4, H2SO4
E) Sia2BH then H2O2
66)
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
67) Name the compound which results when pent-1-yne is treated with sodium in liquid
ammonia.
67)
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68) Provide the IUPAC name for the compound below. 68)
69) What products result when calcium carbide is combined with water? 69)
70) Circle the shortest bond in the compound below. 70)
71) Explain why the synthetic route shown below would be unsuccessful.
HCC:- Na+
1. CH3CH2Br
2. NaNH2 (H3C)3CCCCH2CH3
3. (CH3)3CBr
71)
72) Provide the major organic product of the reaction shown below. 72)
73) Explain why the synthetic route shown below would be unsuccessful.
HCC:- Na+
1. CH3CH2Br
2. NaOCH3 H3CH2CCCCH2CH3
3. CH3CH2I
73)
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74) Provide the major organic product of the reaction shown below. 74)
75) What conditions could be used to isomerize hept-2-yne to hept-1-yne? 75)
76) Provide the major organic product of the reaction shown below. 76)
77) Provide the major organic product of the reaction shown below. 77)
78) Provide the IUPAC name for Cl3C(CH2)3C≡CH. 78)
79) Provide the IUPAC name for (CH3)2CHCH2CH(OH)CH2C≡CCH3. 79)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
80) What is the major organic product that results when 3-heptyne is hydrogenated in the presence of
Lindlar's catalyst?
A) heptane
B) 2-heptyne
C) (Z)-2-heptene
D) (Z)-3-heptene
E) (E)-3-heptene
80)
81) What is the major organic product that results when 3-heptyne is subjected to excess hydrogen and
a platinum catalyst?
A) (E)-3-heptene
B) (Z)-3-heptene
C) (Z)-2-heptene
D) heptane
E) 2-heptyne
81)
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82) What is the major organic product that results when 3-heptyne is treated with sodium metal in
ammonia?
A) (Z)-3-heptene
B) (Z)-2-heptene
C) heptane
D) (E)-3-heptene
E) 2-heptyne
82)
83) What is the major organic product that results when 1-heptyne is treated with 2 equivalents of
HBr?
A) 1,1-dibromoheptane
B) 2,3-dibromo-2-heptene
C) 2,2-dibromoheptane
D) 2,3-dibromo-1-heptene
E) 1,2-dibromoheptane
83)
84) What class of organic product results when 1-heptyne is treated with a mixture of mercuric acetate
in aqueous sulfuric acid?
A) ketone
B) diol
C) ether
D) aldehyde
E) carboxylic acid
84)
85) What class of organic product results when 1-heptyne is reacted with disiamylborane followed by
treatment with basic hydrogen peroxide?
A) aldehyde
B) diol
C) ketone
D) carboxylic acid
E) ether
85)
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
86) What two organic compounds result when 3-heptyne is heated in basic aqueous KMnO4? 86)
87) What two organic compounds result when 3-heptyne is treated with ozone followed by
hydrolysis?
87)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
88) The correct IUPAC name for the following structure is __________.
A) (Z) 4-isopropyl-3-hepten-5-yne B) (Z) 4-isopropyl-4-hepten-2-yne
C) (E) 4-isopropyl-3-hepten-5-yne D) (E) 4-isopropyl-4-hepten-2-yne
88)
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89) What is the correct IUPAC name for the following compound?
A) 4-(1-bromopropyl)-1-hexen-5-yne B) 5-bromo-4-ethynyl-1-heptene
C) 4-allyl-5-bromo-1-hexyne D) 3-(1-bromopropyl)-5-hexen-1-yne
89)
90) Which of the following bases are sufficiently strong to deprotonate a terminal alkyne with an
