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Match the reactions in column I with their reagents in column II. Column I Column II (a) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CHO} \rightarrow \mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCOOH}\) (p) LiAIH \(_{4}\) (b) \(\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{CH}-\mathrm{CHO} \rightarrow \mathrm{CH}_{3} \mathrm{CH}=\mathrm{CH}-\mathrm{CH}_{2} \mathrm{OH}\) (q) \(\mathrm{NaBH}_{4}\) (c) Ph-CH=CH-CHO \(\rightarrow\) Ph-CH \(_{2}-\mathrm{CH}_{2}-\mathrm{CHO}\) (r) \(\mathrm{Pd}-\mathrm{C} / \mathrm{H}_{2}\) (d) \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CH}_{2} \mathrm{CHO} \rightarrow \mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) (s) \(\mathrm{Ag}\left(\mathrm{NH}_{3}\right)_{2}^{\oplus}\)

Short Answer

Expert verified
(a) s, (b) q, (c) r, (d) p

Step by step solution

01

Identify Possible Reactions for Each Option

Begin by identifying what each reagent typically does. 1. 尝颈础濒贬鈧 is a strong reducing agent capable of reducing carbonyls, carboxylic acids, and esters to alcohols. 2. 狈补叠贬鈧 is also a reducing agent, but it is generally milder than 尝颈础濒贬鈧, suitable for reducing aldehydes and ketones to alcohols. 3. Pd-C / H鈧 is used for hydrogenation, typically reducing double or triple bonds. 4. Ag(NH鈧)鈧傗伜 is Tollens' reagent and is used to oxidize aldehydes to carboxylic acids.
02

Analyze Reaction (a)

Observe the transformation from CH鈧-CH鈧=CH-CHO to CH鈧僀H=CHCOOH. This is likely an oxidation reaction of an aldehyde to a carboxylic acid. The reagent suitable for this reaction is Tollens' reagent, Ag(NH鈧)鈧傗伜.
03

Analyze Reaction (b)

In this reaction, CH鈧-CH=CH-CHO is converted to CH鈧僀H=CH-CH鈧侽H. The aldehyde is being reduced to an alcohol. This is a mild reduction, suggesting that 狈补叠贬鈧 is the appropriate reagent.
04

Analyze Reaction (c)

Ph-CH=CH-CHO becomes Ph-CH鈧-CH鈧-CHO. This shows the reduction of the double bond CH=CH to CH鈧-CH鈧 but retains the aldehyde. Hydrogenation, likely with Pd-C / H鈧, suits this transformation.
05

Analyze Reaction (d)

Here, CH鈧=CH-CH鈧侰HO is transformed into CH鈧=CH-CH鈧侰H鈧侽H, indicating the conversion of an aldehyde to an alcohol. Given the strong reducing requirements, 尝颈础濒贬鈧 fits this transformation.
06

Match Each Reaction with Reagents

(a) CH鈧-CH鈧=CH-CHO 鈫 CH鈧僀H=CHCOOH: Ag(NH鈧)鈧傗伜 (oxidation to carboxylic acid) (b) CH鈧-CH=CH-CHO 鈫 CH鈧僀H=CH-CH鈧侽H: 狈补叠贬鈧 (mild reduction to alcohol) (c) Ph-CH=CH-CHO 鈫 Ph-CH鈧-CH鈧-CHO: Pd-C / H鈧 (hydrogenation of double bond) (d) CH鈧=CH-CH鈧侰HO 鈫 CH鈧=CH-CH鈧侰H鈧侽H: 尝颈础濒贬鈧 (reduction to alcohol)

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Key Concepts

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

Reduction Reagents in Organic Chemistry
In organic chemistry, reduction reagents play a crucial role in transforming functional groups by donating electrons. Reduction involves the gain of hydrogen or the loss of oxygen. Typical reduction reagents include lithium aluminium hydride (尝颈础濒贬鈧) and sodium borohydride (狈补叠贬鈧). These reagents are particularly vital for converting carbonyl groups into alcohols.
Reduction is a central theme in synthetic organic chemistry, allowing chemists to selectively reduce specific groups without altering others. This selectivity enables the fine-tuning of molecular structures for desired properties and reactivities.
  • 尝颈础濒贬鈧 is a strong reducing agent used for reducing esters, carboxylic acids, and amides to alcohols.
  • 狈补叠贬鈧 is milder, suitable for converting aldehydes and ketones to alcohols.
Overall, a solid understanding of reduction reagents and their applications is essential for mastering complex organic synthesis tasks.
Oxidation Reagents in Organic Chemistry
Oxidation reagents are another corner of organic chemistry that involves the loss of hydrogen or gain of oxygen. This process is the opposite of reduction. Oxidation reagents like Tollens' reagent are essential for converting alcohols, aldehydes, and other groups into more oxidized states.
One common application is the conversion of aldehydes to carboxylic acids, often using reagents like Tollens' reagent, which is known for its specificity and reliability.
  • Oxidation is critical in extending the functionality of compounds, enabling further chemical reactions.
  • Common oxidation procedures involve not only Tollens' reagent but also other oxidizing agents like KMnO鈧 and CrO鈧, depending on the desired transformation.
Understanding oxidation and reduction reactions provides a balanced view of organic reaction mechanisms, facilitating advanced chemical synthesis.
Hydrogenation
Hydrogenation is a key process in organic chemistry that involves the addition of hydrogen atoms to unsaturated bonds, such as double or triple bonds. This reaction is often carried out in the presence of a catalyst like palladium on carbon (Pd-C), which facilitates the uptake of hydrogen.
Through hydrogenation, alkenes are converted to alkanes, providing a means to "saturate" molecules. This reaction is widely used in the food industry to harden oils, and in fine chemical synthesis, to stabilize structures by replacing reactive unsaturated bonds with more stable single bonds.
  • Hydrogenation helps produce reduced compounds with increased stability.
  • Typical catalysts used include Pd-C, platinum, and nickel, each suiting specific substrates and conditions.
Hydrogenation is a versatile technique that finds broad applications beyond chemistry, impacting the production of everyday products.
Tollens' Reagent
Tollens' reagent is a classical reagent in organic chemistry for the detection and oxidation of aldehydes. It contains complexed silver ions in an aqueous ammonia solution, specifically targeting aldehyde groups.
Its main function is the oxidation of aldehydes to carboxylic acids, resulting in the formation of a silver mirror when aldehydes are oxidized. This silver mirror test is a hallmark of Tollens' reagent, serving as a qualitative analytic tool.
  • Its use is confined to aldehydes; ketones generally do not react.
  • The silver mirror indicates the presence of an aldehyde, providing visual confirmation of the reagent's action.
Tollens' reagent not only emphasizes the chemistry of oxidation but is also indicative of the specificity chemistry can achieve in targeting functional groups.
尝颈础濒贬鈧
Lithium aluminium hydride (尝颈础濒贬鈧) is a powerful reducing agent employed in a wide array of organic transformations. Known for its strength, 尝颈础濒贬鈧 is able to reduce esters, carboxylic acids, and even nitriles to alcohols and amines, respectively.
Despite its potency, care must be taken when using 尝颈础濒贬鈧 as it reacts violently with water, requiring anhydrous conditions for safe handling.
  • 尝颈础濒贬鈧 provides extensive applications in drastically reducing various functional groups.
  • Its reactivity demands careful control, yet its effectiveness in reducing complex structures is renowned.
Its introduction to organic synthesis marked a significant advance, allowing chemists to perform reductions that were previously challenging or impossible.
狈补叠贬鈧
Sodium borohydride (狈补叠贬鈧) is a reducing agent often favored for its mildness compared to 尝颈础濒贬鈧. 狈补叠贬鈧 is primarily used to reduce aldehydes and ketones to alcohols, making it a staple in synthesis whenever sensitive or functionalized molecules are involved.
One of the advantages of 狈补叠贬鈧 is its selectivity and safety, as it can be utilized in aqueous or alcoholic solutions without the explosive risks associated with stronger reducing agents.
  • 狈补叠贬鈧's role is crucial for selective reduction where precision is needed.
  • Its compatibility with mild conditions allows for reductions without adverse reactions with other functional groups.
This reagent is invaluable in both industrial and academic laboratories for its versatility and ease of use.
Pd-C Catalysis
Palladium on carbon (Pd-C) is a prominent catalyst used extensively for hydrogenation reactions. The catalyst facilitates the addition of hydrogen to unsaturated organic compounds, converting double and triple bonds to single bonds.
Pd-C's role extends to a range of transformations, offering chemists the means to control molecular structure via selective saturation of specific unsaturated sites.
  • Pd-C often operates under mild conditions, offering high selectivity.
  • Its efficiency makes it a tool of choice in various applications, from pharmaceutical synthesis to petrochemical processing.
Pd-C catalysis is a testament to how catalytic technology advances the capability of organic transformations, making reactions more efficient and selective for the production of a wide array of chemical products.

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Most popular questions from this chapter

If only one equivalent of \(\mathrm{NH}_{3}\) (one mole of \(\mathrm{NH}_{3}\) reacts with one mole of cyclohexyl chloride) was used, the reaction may not go to completion. Why? (a) \(\mathrm{NH}_{3}\) is not a strong nucleophile. Therefore, more \(\mathrm{NH}_{3}\) is needed. (b) \(\mathrm{Cl}\) is not a good leaving. Therefore, more \(\mathrm{NH}_{3}\) is needed. (c) Cyclohexyl group presents large steric hindrance. Therefore, more \(\mathrm{NH}_{3}\) is needed. (d) \(\mathrm{NH}_{3}\) will be protonated by \(\mathrm{HCl}\) as reaction proceeds. Therefore, the reaction will be incomplete.

What is the structure of 2,4 -hexanedione?

In general, ketones are more reactive towards nucleophiles than esters because (a) The \(\alpha\) -protons of a ketone are more acidic than those of an ester. (b) The alkyl group in a ketone is an electron donating group due to hyperconjugation. (c) Alkoxy (RO-) groups are sterically larger than the related alkyl group. (d) Alkoxy (RO-) groups are stronger electron donating than alkyl groups via resonance.

Which of the following pairs will form the same product with phenyl hydrazine/H (a) \(\mathrm{CH}_{2} \mathrm{OH}-\mathrm{CO}-\mathrm{CH}_{3}\) and \(\mathrm{CHO}-\mathrm{CHOH}-\mathrm{CH}_{3}\) (b) Glucose and mannose (c) Glucose and fructose (d) Glucose and sucrose

\(\mathrm{CH}_{3}-\mathrm{CH}-\mathrm{COOH}\) can be converted into \(\mathrm{CH}_{3}-\mathrm{CH}-\mathrm{CH}_{2} \mathrm{OH}\) by the use of (a) \(\mathrm{H}_{2} / \mathrm{Pd}\) (b) LiAIH \(_{4}\) (c) \(\mathrm{NaBH}_{4}\) (d) \(\mathrm{CH}_{3} \mathrm{MgBr}\)

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