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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
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Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

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Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
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Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

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Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Preparation of Nitriles01:12

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One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
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Additional pitfalls of using 1,1-ADEQUATE for structure elucidation.

Ryan D Cohen1, Josep Saurí2, Chelsea A Huff3,4

  • 1Department of Process Chemistry, Merck Research Laboratories, 126 East Lincoln Ave., Rahway, NJ, 07065, USA. ryan.cohen@merck.com.

Magnetic Resonance in Chemistry : MRC
|July 12, 2016
PubMed
Summary

The 1,1-ADEQUATE NMR experiment efficiently detects carbon-carbon bonds but can show misleading correlations. Researchers highlight potential pitfalls like weak direct couplings and strong multi-bond couplings that may be misinterpreted.

Keywords:
1,1-ADEQUATE3JCC correlationsDFT calculationsINADEQUATEJ-modulated ADEQUATE

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Area of Science:

  • Organic Chemistry
  • Analytical Chemistry
  • Spectroscopy

Background:

  • Nuclear Magnetic Resonance (NMR) spectroscopy is crucial for determining molecular structure.
  • The 1,1-ADEQUATE experiment enhances the detection of carbon-carbon connectivities.
  • Cryogenic probe technology improves NMR sensitivity, enabling experiments with smaller sample sizes.

Purpose of the Study:

  • To investigate potential challenges and limitations of the 1,1-ADEQUATE NMR experiment.
  • To identify specific scenarios where 1,1-ADEQUATE data might be misinterpreted.
  • To provide guidance for accurate interpretation of 1,1-ADEQUATE spectra.

Main Methods:

  • Application of the 1,1-ADEQUATE NMR pulse sequence.
  • Analysis of Nuclear spin-spin coupling constants (JCC).
  • Examination of strongly coupled 13C-13C AB spin systems and specific functional groups.

Main Results:

  • Observed weak or absent direct 1 JCC correlations in strongly coupled 13C-13C AB spin systems.
  • Detected unusually large multi-bond (n JCC) correlations for certain functional groups.
  • Identified potential for misinterpreting large n JCC as direct 1 JCC correlations.

Conclusions:

  • The 1,1-ADEQUATE experiment, while powerful, requires careful interpretation due to potential artifacts.
  • Misinterpretation of spectral data can arise from issues in strongly coupled spin systems and unexpected multi-bond couplings.
  • Awareness of these pitfalls is essential for reliable structural elucidation using 1,1-ADEQUATE NMR.