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For the transformation shown, select the most appropriate reagent(s) to effect the change. For the transformation shown, select the most appropriate reagent(s)  to effect the change.   A)  H<sub>2</sub>SO<sub>4</sub>, HgSO<sub>4</sub>, H<sub>2</sub>O B)  1. Disiamylborane, 2. HO<sup>-</sup>, H<sub>2</sub>O<sub>2</sub> C)  K<sub>2</sub>Cr<sub>2</sub>O<sub>7</sub>, H<sup>+</sup> D)  NaOCl E)  H<sub>2</sub>, Pd


A) H2SO4, HgSO4, H2O
B) 1. Disiamylborane, 2. HO-, H2O2
C) K2Cr2O7, H+
D) NaOCl
E) H2, Pd

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Provide the reagent(s) expected to accomplish the transformation shown below: Provide the reagent(s) expected to accomplish the transformation shown below:

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H2, Ni2B or ...

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Which of the compounds shown below would be the most likely product expected from the reaction scheme shown? Which of the compounds shown below would be the most likely product expected from the reaction scheme shown?   A)  I B)  II C)  III D)  IV E)  V


A) I
B) II
C) III
D) IV
E) V

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Which of the following is a structure for hepta-3,6-dien-1-yne? Which of the following is a structure for hepta-3,6-dien-1-yne?   A)  I B)  II C)  III D)  IV E)  V


A) I
B) II
C) III
D) IV
E) V

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Select the expected major product(s) from the treatment of 1-pentyne with 1 equivalent of HBr in the presence of peroxides.


A) 2-bromo-1-pentene
B) (E) -1-bromo-1-pentene
C) (Z) -1-bromo-1-pentene
D) A and B
E) B and C

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Provide the IUPAC name for Cl3C(CH2) 4C≡CH.


A) 4,4,4-trichloro-1-butyne
B) 1,1,1-trichloro-6-heptyne
C) 1,1,1-trichloro-5-heptyne
D) 6,6,6-trichloro-1-hexyne
E) 7,7,7-trichloro-1-heptyne

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What is the expected major product of the reaction sequence shown below? What is the expected major product of the reaction sequence shown below?   A)  I B)  II C)  III D)  IV E)  V


A) I
B) II
C) III
D) IV
E) V

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For the reaction below, select the structure of the major organic product. For the reaction below, select the structure of the major organic product.   A)  I B)  II C)  III D)  IV E)  V


A) I
B) II
C) III
D) IV
E) V

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What reagent(s) are required to prepare trans-2-heptene from 2-heptyne?

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Which of the following methods would be expected to efficiently produce cis-2-butene as the major organic product?


A) CH3CHBrCH2CH3 + (CH3) 3COK/(CH3) 3COH
B) CH3C≡CCH3 + H2, Pt
C) CH3C≡CCH3 + H2, Ni2B (P-2)
D) CH3C≡CCH3 + Na, NH3(l)
E) CH3CHBrCH2CH3 + NaNH2

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For the reaction shown, select the expected major organic product. For the reaction shown, select the expected major organic product.   A)  I B)  II C)  III D)  IV E)  V


A) I
B) II
C) III
D) IV
E) V

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Provide the IUPAC name for CH3C≡CC(CH3)2CH(CH2CH3)2.

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5-ethyl-4,4-dimethyl...

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What is the IUPAC name for the molecule shown below? What is the IUPAC name for the molecule shown below?   A)  1,1-diethyl-2-pentyne B)  3-(1-butynyl) pentane C)  5-ethyl-3-octyne D)  3-ethyl-4-heptyne E)  5-ethyl-3-heptyne


A) 1,1-diethyl-2-pentyne
B) 3-(1-butynyl) pentane
C) 5-ethyl-3-octyne
D) 3-ethyl-4-heptyne
E) 5-ethyl-3-heptyne

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Provide the IUPAC name for CH3CH(CH3)C(CH3)2C≡CCH(CH3)2.

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2,5,5,6-tetramethyl-...

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For the reaction shown below, the resulting stereochemistry of the expected product is best described as: For the reaction shown below, the resulting stereochemistry of the expected product is best described as:   A)  only (S)  B)  only (R)  C)  racemic D)  meso E)  achiral


A) only (S)
B) only (R)
C) racemic
D) meso
E) achiral

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Which of the bases below would quantitatively deprotonate a terminal alkyne?


A) BuLi
B) NH3
C) NaOH
D) NaOCH2CH3
E) t-BuOK

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Reaction of 3,4,5-trimethyl-4-hexen-1-yne with H2 and Pd/C will produce which of the following compounds?


A) 2,3,4-trimethylhexane
B) 3,4,5-trimethylhexane
C) 2,3,4-trimethyl-1-hexene
D) 3,4,5-trimethyl-1-hexyne
E) 2,3,4-trimethyl-5-hexyne2

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For the reaction below, select the structure of the expected major organic product. For the reaction below, select the structure of the expected major organic product.   A)  I B)  II C)  III D)  IV E)  V


A) I
B) II
C) III
D) IV
E) V

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Of the species listed below, select those less basic than acetylide.


A) BuLi
B) NaNH2
C) NaOCH3
D) both A and C
E) both B and C

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For the reaction shown, which of the compounds below would be the expected major, and final, organic product? For the reaction shown, which of the compounds below would be the expected major, and final, organic product?   A)  I B)  II C)  III D)  IV E)  V


A) I
B) II
C) III
D) IV
E) V

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