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Chapter 12: Q.68. (page 493)

Question:Devise a synthesis of (3R,4S)-3,4-dichlorohexane from acetylene and any needed organic compounds or inorganic reagents.

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01

Conversion of acetylene to hex-3-yne

Acetylene can be converted to acetylide anion upon treatment with a strong base, which makes them a reagent for nucleophilic substitution.

Based on this theory, acetylene is converted to hex-3-yne as shown below:

Formation of hex-3-yne from acetylene

02

Synthesis of (3R,4S)-3,4-dichlorohexane from hex-3-yne

Hex-3-yne can be treated with sodium in liquid ammonia to reduce it to hex-3-ene via anti-addition of hydrogen. Further anti-addition of chlorine to the alkene leads to the formation of(3R,4S)-3,4-dichlorohexane.The reaction is given below:

Synthesis of(3R,4S)-3,4-dichlorohexane from hex-3-yne

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Most popular questions from this chapter

Question: Draw all stereoisomers formed when each alkene is treated with mCPBA.

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Question: Draw the organic products formed when each alkene is treated with H2 / Pd-C. Indicate the three-dimensional structure of all stereoisomers formed.

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Question: Draw the products formed when each alkyne is treated with O3 followed by H2O .

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Question: It is sometimes necessary to isomerize a cis alkene to a trans alkene in a synthesis, a process that cannot be accomplished in a single step. Using the reactions that you have learned in Chapters 8–12, devise a stepwise method to convert cis-but-2-ene to trans-but-2-ene.

Question: Sharpless epoxidation of allylic alcohol X forms compound Y. Treatment of Y with NaOH and C6H5SH in an alcohol–water mixture forms Z. Identify the structure of Y and draw a mechanism for the conversion of Y to Z. Account for the stereochemistry of the stereogenic centers in Z. Z has been used as an intermediate in the synthesis of chiral carbohydrates.
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