Skip to main content
Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Non è quello che usi tu?Cambia libro di testo
Capitolo 9, Problema 26c

Suggest alkynes that might be used to make the following trans-alkenes.
(c) Chemical reaction diagram showing sodium and liquid ammonia at -33°C producing a specific trans-alkene structure with deuterium.

Guida verificata passo dopo passo
1
Identify the trans-alkene product structure. A trans-alkene has two substituents on opposite sides of the double bond. Analyze the given trans-alkene to determine the carbon chain and substituents.
Recall that alkynes can be reduced to trans-alkenes using a dissolving metal reduction, such as sodium (Na) in liquid ammonia (NH₃). This reaction selectively produces trans-alkenes from alkynes.
Determine the alkyne precursor by adding a triple bond in place of the double bond in the trans-alkene. This involves identifying the two carbons involved in the double bond and converting it into a triple bond.
Ensure that the alkyne precursor has the correct number of carbons and substituents to match the trans-alkene product after reduction. Verify that the structure of the alkyne aligns with the desired trans-alkene.
Propose the alkyne(s) that could be used as starting materials. For example, if the trans-alkene has substituents on opposite sides, the corresponding alkyne should have the same substituents attached to the triple bond carbons.

Risposta video verificata per un problema simile:

Questa soluzione video è stata consigliata dai nostri tutor come utile per risolvere questo problema.
Durata del video:
3m

Concetti chiave

Ecco i concetti essenziali che devi comprendere per rispondere correttamente alla domanda.

Alkynes

Alkynes are hydrocarbons that contain at least one carbon-carbon triple bond. They are unsaturated compounds and are represented by the general formula CnH2n-2. Alkynes can undergo various reactions, including addition reactions, which are crucial for synthesizing other organic compounds, such as alkenes and alcohols.
Video consigliato:
09:11
Alkyne Hydration

Trans-Alkenes

Trans-alkenes are a type of alkene where the substituents on either side of the double bond are positioned on opposite sides, leading to a more stable configuration due to reduced steric strain. The geometric isomerism in alkenes is significant in organic chemistry, as it affects the physical and chemical properties of the compounds.
Video consigliato:
Percorso guidato
3:04
Alkene Metathesis Example 2

Elimination Reactions

Elimination reactions involve the removal of atoms or groups from a molecule, resulting in the formation of a double or triple bond. In the context of synthesizing trans-alkenes from alkynes, a common method is the partial hydrogenation of alkynes or the elimination of a leaving group from a precursor compound, which can yield the desired trans configuration.
Video consigliato:
00:40
Recognizing Elimination Reactions.