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Chapter 12: Problem 23

What alkyne (or diyne) yields each set of oxidative cleavage products? a. \(CO_2 + CH_3(CH_2)_8C0_2H\) c. \(CH_3CH_2C0_2H\), \(HO_2CCH_2C0_2H, CH_3CO_2H\) b. \(CH_3CH_2CH(CH_3)CO_2H\) only d. \(H0_2C(CH_2)_14CO_2H\)

Short Answer

Expert verified
a. HC鈮(CH鈧�)鈧圕H鈧�, b. CH鈧僀H鈧侰鈮CH(CH鈧�)CH鈧�, c. CH鈧僀鈮C鈮CH鈧侰H鈧�, d. HC鈮(CH鈧�)鈧佲倓C鈮H.

Step by step solution

01

Understand Oxidative Cleavage

Oxidative cleavage of alkynes breaks the triple bond to form carboxylic acids. For terminal alkynes, one product is a carboxylic acid and CO鈧�. For internal alkynes, two carboxylic acids are formed.
02

Analyze Product Set a

Product set a gives CO鈧� and a carboxylic acid. This suggests the cleavage of a terminal alkyne. By considering the structure, the alkyne is likely \(HC \equiv C(CH_2)_8CH_3\). After cleavage, this alkyne gives CO鈧� from the terminal carbon and CH鈧�(CH鈧�)鈧圕O鈧侶 from the remaining chain.
03

Analyze Product Set b

Product set b shows a single carboxylic acid. This indicates cleavage of a symmetrical internal alkyne. The oxidation product suggests the alkyne \(CH_3CH_2C \equiv CCH(CH_3)CH鈧僜) after oxidative cleavage yields the product CH鈧僀H鈧侰H(CH鈧�)CO鈧侶.
04

Analyze Product Set c

Product set c yields three carboxylic acids, indicating an internal diyne. By analyzing possible structures, one can conclude that CH鈧僀\(\equiv\)CC\(\equiv\)CCH鈧侰H鈧� provides all given products after oxidative cleavage.
05

Analyze Product Set d

Product set d results in a single symmetrical dicarboxylic acid, indicating an internal alkyne in a symmetrical structure. This suggests the alkyne \(HC \equiv C(CH_2)_{14}C \equiv CH\), providing the given dicarboxylic acid H0鈧侰(CH鈧�)鈧佲倓CO鈧侶.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Alkynes
Alkynes are hydrocarbons that contain at least one carbon-carbon triple bond, giving them the general formula \(C_nH_{2n-2}\). The presence of this triple bond is a key feature that defines alkynes and differentiates them from alkanes and alkenes, which contain single and double bonds, respectively. The chemical reactivity of alkynes is primarily attributed to this triple bond.
  • Triple bonds consist of one sigma bond and two pi bonds, which are more reactive compared to single or double bonds.
  • Alkynes can undergo a variety of chemical reactions, such as hydrogenation, hydrohalogenation, and oxidative cleavage.
Understanding the distinct properties and reactions of alkynes is crucial in organic chemistry, especially their ability to form carboxylic acids through oxidative cleavage.
Carboxylic Acids
Carboxylic acids are a class of organic compounds characterized by the presence of a carboxyl group, \(-COOH\). These compounds are highly important in both biological and industrial contexts due to their wide range of chemical properties. The carboxyl group consists of a carbon atom double-bonded to an oxygen atom and single-bonded to a hydroxyl group.
  • Carboxylic acids are weak acids, meaning they can donate a proton \(H^+\) in a solution.
  • They can form hydrogen bonds, which significantly contribute to their solubility in water.
A significant reaction involving carboxylic acids is their formation from alkynes via oxidative cleavage, where the triple bond of the alkyne is broken down to yield these acids as products.
Internal Alkynes
Internal alkynes are a specific type of alkyne where the triple bond is located between two carbon atoms that are within the carbon chain, meaning neither carbon in the triple bond is a terminal carbon. As a result of their structure, the main oxidative cleavage products of internal alkynes are two carboxylic acids.
  • Internal alkynes tend to be symmetrical, making it easier to predict the products of their oxidative cleavage.
  • The cleavage breaks both pi bonds in the triple bond, resulting in the formation of two separate carboxyl groups on each carbon of the alkyne.
Recognizing internal alkyne structures helps predict the resulting carboxylic acids after the oxidative process, which is key in chemical analysis and synthesis.
Terminal Alkynes
Terminal alkynes feature the triple bond at the end of the carbon chain, with one carbon of the triple bond being connected to a hydrogen atom. During oxidative cleavage, terminal alkynes generate different products compared to internal alkynes.
  • The terminal carbon, bonded to the hydrogen, typically forms carbon dioxide (CO鈧�) after the alkyne is cleaved.
  • The remaining carbon chain after the triple bond results in a carboxylic acid.
This distinct product formation makes terminal alkynes identifiable. Understanding the structural difference and the resultant products from oxidative cleavage is vital in solving organic chemistry problems and realizing synthetic pathways.

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Most popular questions from this chapter

Devise a synthesis of each compound from \(CH_3CH_20H\) as 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.

Draw the products formed when both cis- and trans-2-butene are treated with \(4Os0_4\), followed by hydrolysis with \(NaHS0_3\) \(+ H_20\). Explain how these reactions illustrate that syn dihydroxylation is stereospecific.

Stearidonic acid (\(C_{18}H_{28}O_2\)) is an unsaturated fatty acid obtained from oils isolated from hemp and blackcurrant (see also Problem 10.11 ). a. What fatty acid is formed when stearidonic acid is hydrogenated with excess H\(_2\) and a Pd catalyst? b. What fatty acids are formed when stearidonic acid is hydrogenated with one equivalent of H\(_2\) and a Pd catalyst? c. Draw the structure of a possible product formed when stearidonic acid is hydrogenated with one equivalent of \(H_2\) and a Pd catalyst, and one double bond is isomerized to a trans isomer. d. How do the melting points of the following fatty acids compare: stearidonic acid; one of the products formed in part (b); the product drawn in part (c)?

Devise a synthesis of each compound from acetylene and organic compounds containing two carbons or fewer. You may use any other required reagents.

How many rings and n bonds are contained in compounds \(A-C\)? Draw one possible structure for each compound. a. Compound \(A\) has molecular formula \(C_5H_8\) and is hydrogenated to a compound having molecular formula \(C_5H_{10}\). b. Compound \(B\) has molecular formula \(C_{10}H_{16}\) and is hydrogenated to a compound having molecular formula \(C_{10}H_{18}\). c. Compound \(C\) has molecular formula \(C_8H_8\) and is hydrogenated to a compound having molecular formula \(C_8H_{16}\).
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