A proton transfer reaction can occur when an aldehyde is placed in strong base, such as an alkoxide ion, producing an alcohol and a charged conjugate base that is resonance stabilized. In the left box, draw the curved arrows for the proton transfer. In the middle and right boxes, draw the two structures for the resonance-stabilized product as noted in the box-specific directions. Be sure to include all lone pairs and nonzero formal charges. **Reaction Mechanism: Proton Transfer Between Aldehyde and Alkoxide Ion****Instructions:**Draw curved arrows to illustrate the proton transfer reaction between the aldehyde and the alkoxide ion.**Diagram Explanation:**1. **Initial Structure:** - The diagram depicts an aldehyde with the structure: \[ \begin{array}{c} \text{O} \\ || \\ \text{C}-\text{H} \\ | \\ \text{H} \end{array} \] - The alkoxide ion is shown as: \[ \text{O}^{-}-\text{CH}_3 \]2. **Components:** - The aldehyde features a carbonyl group (C=O) with two lone pairs on the oxygen atom. - The alkoxide ion has a negatively charged oxygen (with three lone pairs) bonded to a methyl group (CH₃).**Reaction Process:**- The alkoxide ion donates its lone pair (curved arrow) to the hydrogen of the aldehyde's hydrogen atom.- Simultaneously, a pair of electrons from the C-H bond of the aldehyde relocates to the carbonyl oxygen, forming another lone pair and neutralizing the charge on the oxygen.Understanding proton transfer reactions is essential for studying acid-base chemistry and mechanisms in organic reactions. This demonstration showcases how electron pairs move in such reactions, highlighting roles like nucleophiles (electron pair donors) and electrophiles (electron pair acceptors).

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Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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A proton transfer reaction can occur when an aldehyde is placed in strong base, such as an alkoxide ion, producing an alcohol and a charged conjugate base that is resonance stabilized. In the left box, draw the curved arrows for the proton transfer. In the middle and right boxes, draw the two structures for the resonance-stabilized product as noted in the box-specific directions. Be sure to include all lone pairs and nonzero formal charges.

**Reaction Mechanism: Proton Transfer Between Aldehyde and Alkoxide Ion**

**Instructions:**
Draw curved arrows to illustrate the proton transfer reaction between the aldehyde and the alkoxide ion.

**Diagram Explanation:**

1. **Initial Structure:**
- The diagram depicts an aldehyde with the structure:
\[
\begin{array}{c}
\text{O} \\
|| \\
\text{C}-\text{H} \\
| \\
\text{H}
\end{array}
\]
- The alkoxide ion is shown as:
\[
\text{O}^{-}-\text{CH}_3
\]

2. **Components:**
- The aldehyde features a carbonyl group (C=O) with two lone pairs on the oxygen atom.
- The alkoxide ion has a negatively charged oxygen (with three lone pairs) bonded to a methyl group (CH₃).

**Reaction Process:**
- The alkoxide ion donates its lone pair (curved arrow) to the hydrogen of the aldehyde's hydrogen atom.
- Simultaneously, a pair of electrons from the C-H bond of the aldehyde relocates to the carbonyl oxygen, forming another lone pair and neutralizing the charge on the oxygen.

Understanding proton transfer reactions is essential for studying acid-base chemistry and mechanisms in organic reactions. This demonstration showcases how electron pairs move in such reactions, highlighting roles like nucleophiles (electron pair donors) and electrophiles (electron pair acceptors).

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

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