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When pent-2-yne reacts with mercuric sulfate in dilute sulfuric acid, the product is a mixture of two ketones. Give the structures of these products, and use mechanisms to show how they are formed.

Short Answer

Expert verified

Ketone is the organic compound with a carbonyl functional group with a carbon attack to double bond oxygen (C=O). The chain is attached to two carbon groups at either side of carbonyl carbon.

Ketones are important in biochemistry and drug treatment used in anti-inflammatory medication.

Step by step solution

01

Step-by-Step SolutionStep 1: Ketone

Ketone is the organic compound with a carbonyl functional group with a carbon attack to double bond oxygen (C=O). The chain is attached to two carbon groups at either side of carbonyl carbon.

Ketones are important in biochemistry and drug treatment used in anti-inflammatory medication.

02

 Forming a mixture of two ketone

The reaction of pent-2-yne with a mixture of mercuric sulfate in dilute sulfuric acid hydration reaction happen which initially give vinyl alcohol that quickly rearranges to give the mixture of two ketones: pent-3-one and pent-2-one

Formation of the mixture of ketone

03

Mechanism of the reaction forming mixture of two ketone

Electrophile addition of mercuric ion gives a vinyl cation. There is the possibility of forming two carbocations ( 20vinyl carbocation). Both react with water and lose a proton to give organomercurial alcohol.

Formation of organomercurial alcohol

Under the acidic condition, H+from H2SO4, mercury is replaced by hydrogen to give vinyl alcohol called enol, which is unstable form. Thus, isomerize to the keto form giving the mixture of ketone pent-3-one and pent-2-one.

Mechanism showing the formation of a mixture of ketone

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Most popular questions from this chapter

The fragrance of (Z)-1-phenylhex-2-en-1-ol resembles that of roses, with a delicate citrus edge. Show how you would synthesize this compound from benzaldehyde (PhCHO) and any other reagents you need.

Question:Show how you would accomplish the following synthetic transformations. Show all intermediates.

(²¹)2,2-»å¾±²ú°ù´Ç³¾´Ç²ú³Ü³Ù²¹²Ô±ð→b³Ü³Ù-1-²â²Ô±ð

(²ú)2,2-»å¾±²ú°ù´Ç³¾´Ç²ú³Ü³Ù²¹²Ô±ð→b³Ü³Ù-2-²â²Ô±ð

(³¦)²ú³Ü³Ù-1-²â²Ô±ð→o³¦³Ù-3-²â²Ô±ð

(d)trans-³ó±ð³æ-2-±ð²Ô±ð→h±ð³æ-2-²â²Ô±ð

(±ð)2,2-»å¾±²ú°ù´Ç³¾´Ç³ó±ð³æ²¹²Ô±ð→h±ð³æ-1-²â²Ô±ð

(´Ú)³¦²â³¦±ô´Ç»å±ð³¦²â²Ô±ð→cis-cyclodecene

(²µ)³¦²â³¦±ô´Ç»å±ð³¦²â²Ô±ð→trans-cyclodecene

(h)hex-1-yne→hexan-2-one, CH3COCH2CH2CH2CH3

(i)hex-1-yne→hexanal, CH3(CH2)4CHO

(j)trans-³ó±ð³æ-2-±ð²Ô±ð→cis-hex-2-ene

The boiling points of hex-1-ene (64 °C) and hex-1-yne (71 °C) are sufficiently close that it is difficult to achieve a clean separation by distillation. Show how you might use the acidity of hex-1-yne to remove the last trace of it from a sample of hex-1-ene.

Propose a mechanism for the reaction of pent-1-yne with HBr in the presence of peroxides. Show why anti-Markovnikov orientation results.

Question:When treated with hydrogen and a platinum catalyst, an unknown compound X absorbs 5 equivalents of hydrogen to give n-butylcyclohexane. Treatment of X with an excess of ozone, followed by dimethyl sulfide and water, gives the following products:

Propose a structure for the unknown compound X. Is there any uncertainty in your structure?

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