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Which sequence of reagents will accomplish the following synthesis? Which sequence of reagents will accomplish the following synthesis?   A)  1. KOtBu; 2. 1-bromopropane B)  1. NaNH<sub>2</sub>; 2. 1-bromopropane C)  1. NaNH<sub>2</sub>; 2. 2-bromopropane D)  1. O<sub>3</sub>; 2. DMS E)  1. O<sub>3</sub>; 2. 1-bromopropane


A) 1. KOtBu; 2. 1-bromopropane
B) 1. NaNH2; 2. 1-bromopropane
C) 1. NaNH2; 2. 2-bromopropane
D) 1. O3; 2. DMS
E) 1. O3; 2. 1-bromopropane

F) B) and E)
G) None of the above

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Perform a retrosynthetic analysis by working backwards two steps in the synthesis below. Identify possible combinations of A and B that can lead to the alkyne (C) . Perform a retrosynthetic analysis by working backwards two steps in the synthesis below. Identify possible combinations of A and B that can lead to the alkyne (C) .       A)  B = I and A = VI B)  B = VI and A = I C)  B = III and A = VII D)  B = IV and A = VII E)  B = VI and A = VIII Perform a retrosynthetic analysis by working backwards two steps in the synthesis below. Identify possible combinations of A and B that can lead to the alkyne (C) .       A)  B = I and A = VI B)  B = VI and A = I C)  B = III and A = VII D)  B = IV and A = VII E)  B = VI and A = VIII Perform a retrosynthetic analysis by working backwards two steps in the synthesis below. Identify possible combinations of A and B that can lead to the alkyne (C) .       A)  B = I and A = VI B)  B = VI and A = I C)  B = III and A = VII D)  B = IV and A = VII E)  B = VI and A = VIII


A) B = I and A = VI
B) B = VI and A = I
C) B = III and A = VII
D) B = IV and A = VII
E) B = VI and A = VIII

F) B) and E)
G) A) and C)

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Devise a synthetic route to convert 5-methyl-1-hexene into 5-methylhexanal.

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Select the best reagents for the reaction below. Select the best reagents for the reaction below.   A)  1. OsO<sub>4</sub>; 2. NaHSO<sub>3</sub>, H<sub>2</sub>O B)  1. Hg(OAc) <sub>2</sub>, H<sub>2</sub>O; 2. NaBH<sub>4</sub> C)  1. RCO<sub>3</sub>H; 2. H<sub>3</sub>O<sup>+</sup> D)  H<sub>2</sub>SO<sub>4</sub>, H<sub>2</sub>O E)  1. O<sub>3</sub>; 2. DMS


A) 1. OsO4; 2. NaHSO3, H2O
B) 1. Hg(OAc) 2, H2O; 2. NaBH4
C) 1. RCO3H; 2. H3O+
D) H2SO4, H2O
E) 1. O3; 2. DMS

F) A) and E)
G) B) and C)

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Which of the following sequences of reagents will move the alcohol functional group from the tertiary position of 1-methylcyclohexanol to a secondary position?


A) 1. KOtBu; 2. Hg(OAc) 2, H2O; 3. NaBH4
B) 1. TsCl, pyr; 2. KOtBu; 3. BH3-THF; 4. H2O2, NaOH
C) 1. H2SO4, heat; 2. BH3∙THF; 3. H2O2, NaOH
D) 1. TsCl, pyr; 2. NaOH; 3. BH3∙THF; 4. H2O2, NaOH
E) C and D will both work

F) A) and D)
G) C) and D)

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Select the best reagents for the reaction below. Select the best reagents for the reaction below.   A)  1. OsO<sub>4</sub>; 2. NaHSO<sub>3</sub>, H<sub>2</sub>O B)  H<sub>2</sub>SO<sub>4</sub>, H<sub>2</sub>O, HgSO<sub>4</sub> C)  H<sub>2</sub>, Pt D)  1. 9-BBN; 2. H<sub>2</sub>O<sub>2</sub>, NaOH E)  1. O<sub>3</sub>; 2. DMS


A) 1. OsO4; 2. NaHSO3, H2O
B) H2SO4, H2O, HgSO4
C) H2, Pt
D) 1. 9-BBN; 2. H2O2, NaOH
E) 1. O3; 2. DMS

F) C) and D)
G) A) and C)

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