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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: Devise a synthesis of each compound from CH3CH2OHas the only organic starting material; that is, every carbon in the product must come from a molecule of ethanol. You may use any other needed inorganic reagents.

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Question: What product is formed when CH3OCH2CH2C鈮�CCH2CHCH32 is treated with each reagent: (a) H2 (excess), Pd-C; ; (b) H2(1 equiv), Lindlar catalyst; (c) H2(excess), Lindlar catalyst; (d) Na,NH3 ?

Question: Draw the products formed when each diene is treated with O3 followed by CH3SCH3.

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Question: Draw the organic products formed when allylic alcohol A is treated with each reagent.

a. H2 +Pd-c

b. mCPBA

c. PCC

d. CrO3 ,H2SO4, H2O

e.(CH3)3COOH , Ti [OCH(CH3)3]4 (+) -DET

f.(CH3)3COOH , Ti [OCH(CH3)3]4 (-) -DET

g. [1] PBr3,[2] LiAlH4 ,[3] H2O

h. HCrO4- 鈥揂mberlyst A-26 resin
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