Folder test bank is orgo chapter 9 ne wa
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In organic chemistry, an alkyne is an unsaturated hydrocarbon which has at least one carbon—carbon triple bond between two carbon atoms.[1] The simplest acyclic alkynes with only one triple bond and no other functional groups form a homologous series with the general chemical formula CnH2n-2. Alkynes are traditionally known as acetylenes, although the name acetylene also refers specifically to C2H2, known formally as ethyne using IUPAC nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic but tend to be more reactive
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Question 1 (Alcohols and Carbonyl Compounds - 20 marks)
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O OH
(2)
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HHO
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OHH
HHO
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(2)
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(2)
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(3)
4
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A. B.
C.
O
HO
HO
OH
O
OH
O
HO
OH
O
HO
OH
O
O
HO2C
OH OH
(i) Use arrows to identify the glycoside links between sugars a and b as well as b and
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(2)
5
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weight.
(2)
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N
(1)
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(1)
(c) Give the outcome of the reactions below.
(i) Ph-NH2 + CH3-CO2H
(1)
(ii)
H3O
+
N
H
O
(2)
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N
H
O
Predict the solubility of N-methylpropanamide by showing the full extent of H-
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(2)
6
(e) Explain with refe ...
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1
Question 1 (Alcohols and Carbonyl Compounds - 20 marks)
(a) Why does hexan-2-one have a lower boiling point than hexan-2-ol?
O OH
(2)
(b) Dehydration of the compound below in acid gives mainly one product. Suggest, with a
reason, what would be the major product.
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+
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(1)
(c) Esters are known for their very pleasant fragrances. The aroma is dependent on the
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(ii) Which factor can be investigated to determine if the reaction proceeds by a
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mechanism?
(2)
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(4)
3
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CHO
HHO
OHH
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HHO
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(2)
(iii) When the compound is reduced with NaBH4, is the product optically active or
not? Explain your answer.
(2)
(b) What is the process called when the optical rotation of an aqueous solution of a pure
anomer of glucose changes with time? Use chemical structures to demonstrate what is
happening.
(3)
4
(c) The following question relates to the structure below:
A. B.
C.
O
HO
HO
OH
O
OH
O
HO
OH
O
HO
OH
O
O
HO2C
OH OH
(i) Use arrows to identify the glycoside links between sugars a and b as well as b and
c and name them appropriately.
(3)
(ii) Explain if this is a reducing sugar or not.
(2)
5
Question 3 (Amines and Amides - Total 11 marks)
(a) Briefly explain why amines have lower boiling points than amides of similar molecular
weight.
(2)
(b) (i) What is the name of the following amine?
N
(1)
(ii) What is the structure of 2,2-dimethylpentanamine?
(1)
(c) Give the outcome of the reactions below.
(i) Ph-NH2 + CH3-CO2H
(1)
(ii)
H3O
+
N
H
O
(2)
(d) The structure of N-methylpropanamide is given below.
N
H
O
Predict the solubility of N-methylpropanamide by showing the full extent of H-
bonding between the compound and water.
(2)
6
(e) Explain with refe ...
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- 2. • 1. What is the IUPAC name of the following compound? • • • • A. B. C. D. 5-propyl-3-heptyne 5-isopropyl-3-heptyne 5-ethyl-3-octyne 4-ethyl-5-octyne
- 3. • 2. Which of the following describes the orbital overlap of the C(1) - C(2) sigma bond of 1butyne, shown below? • • • • A. B. C. D. sp-sp sp2-sp2 sp3-sp3 2p-2p
- 4. • 3. Which of the following gives only one organic product on ozonolysis? • • • • A. B. C. D. 2-hexene 3-hexene 2-heptene 3-heptene
- 5. 4. What is the IUPAC name of the following compound? • • • • A. B. C. D. 2-methyl-5-propyl-3-heptyne 1-isopropyl-3-propyl-1-pentyne 5-ethyl-2-methyl-3-octyne 4-ethyl-7-methyl-5-octyne
- 6. • 5. Which one of the following describes the C(2)-C(3) sigma bond in the structure below? • • • • A. B. C. D. sp-sp sp2-sp2 sp3-sp3 2p-2p
- 7. • 6. Select the best base to quantitatively remove a proton from acetylene. • • • • A. B. C. D. NaNH2 NH3 NaOH NaOCH2CH3
- 8. 7. Arrange the following in order of decreasing base strength (strongest base first). • • • • A. B. C. D. IV > III > II > I II > III > I > IV I > II > IV > III II > III > IV > I
- 9. 8. Predict the major product(s) in the reactions below. • • • • • A. B. C. D. 1-nonyne 2-nonyne cis-2-nonene trans-2-nonene
- 10. • 10. Which sequence of reactions works best in synthesizing cis-3-nonene? • • • • A. B. C. D. A B C D
- 11. • 11. Which sequence of reactions below works best in carrying out the following conversion? • • • • A. B. C. D. (1) HBr (1) Br2 (1) Br2, H2O (1) H2O, H2SO4(cat.) (2) excess NaNH2 (2) excess NaNH2 (2) excess NaNH2 (2) excess NaNH2
- 12. • 12. Which of the following is the enol intermediate in the acid-catalyzed addition of water to propyne? • • • • A. B. C. D. A B C D
- 13. 13. Which reagent below would be used to convert 2-pentyne to trans-2-pentene? • • • • A. B. C. D. NaNH2, NH3 Na, NH3 H2, Lindlar Pd H2O, HgSO4/H2SO4
- 14. 14. Select the best method to carry out the following conversion. • • • • A. B. C. D. A B C D
- 15. 15. Which of the following is the correct IUPAC name of the product for the reaction shown below? • • • • A. B. C. D. cis-2-methyl-5-heptene trans-2-methyl-5-heptene cis-6-methyl-2-heptene trans-6-methyl-2-heptene
- 16. • 16. Identify compound Y. • A. 2-bromobutane • B. meso-2,3-dibromobutane • C. racemic (2R,3R) and (2S,3S)-2,3dibromobutane • D. 2,3-dibromo-2-butene
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- 18. 18. When alkynes are treated with sodium metal, Na, in liquid ammonia, sodium acts as a • • • • A. B. C. D. Brønsted acid. Brønsted base. reducing agent. catalyst.
- 19. • 19. Select the best reaction sequence to make the following ketone. • • • • A. B. C. D. A B C D