For A & B, you MAY NOT add or erase lone pairs. H3C H,C-CHCH2 А. H2N. `CH „NH2 HC Н—С—СН- -C-H Hint: Make N charged. Also, do one side at a time, but dont do both sides at В. the same time. NH2 HC CH H-C-CH- -C-H Alternatively, we can also have: H2N. `CH NH2 HC H-C- Н—С—СН—с—н

Organic Chemistry: A Guided Inquiry
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ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
ChapterL2: Mass Spectrometry
Section: Chapter Questions
Problem 20CTQ
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Provide ALL reasonable resonance structures for each molecular structure below. Note that you need use the curved arrows to show how electrons are moved and please make sure your answers are legit Lewis structure (with lone pairs).

### Resonance Structures Practice

For A & B, you MAY NOT add or erase lone pairs.

#### A.
\[ \text{H}_3\text{C}-\overset{\overset{\cdot\cdot}{\cdot}\cdot}{\text{C}}\text{H}-\overset{\overset{\cdot\cdot}{\cdot}\cdot}{\text{C}}=\text{C}\text{H}_2 \rightleftharpoons \]

Here you are given a structure with a carbon chain and implied resonance directions. Try to depict alternative resonance structures while maintaining the lone pairs as they are.

#### B.
\[ \begin{aligned}
\text{H}_2\text{N} & = \overset{\overset{\cdot\cdot}{\cdot}\cdot}{\text{C}}-\text{H} \\
& \| \\
& \text{C}=\text{C}-\text{H} \\
& \| \\
& \text{N}\text{H}_2 \quad \rightleftharpoons \\
\end{aligned} \]


##### Hint: 
Make N charged. Also, do one side at a time, but don't do both sides at the same time.

\[ \begin{aligned}
\text{H}_2\text{N} & \equiv \overset{+}{\text{C}}-\text{H} \\
& \| \\
& \text{C}=\text{C}-\text{H} \\
& \| \\
& \text{N}\text{H}_2 \quad \rightleftharpoons \\
\end{aligned} \]

Alternatively, we can also have:

\[ \begin{aligned}
\text{H}_2\text{N} & = \overset{\overset{\cdot\cdot}{\cdot}\cdot}{\text{C}}-\text{H} \\
& \| \\
& \text{C}-\text{C}-\text{H} \\
& \| \\
& \text{N}\text{H}_2 \quad \\
\end{aligned} \]


This problem requires adjusting molecular structures to show resonance forms. Follow the guidelines to ensure lone pairs remain unaltered,
Transcribed Image Text:### Resonance Structures Practice For A & B, you MAY NOT add or erase lone pairs. #### A. \[ \text{H}_3\text{C}-\overset{\overset{\cdot\cdot}{\cdot}\cdot}{\text{C}}\text{H}-\overset{\overset{\cdot\cdot}{\cdot}\cdot}{\text{C}}=\text{C}\text{H}_2 \rightleftharpoons \] Here you are given a structure with a carbon chain and implied resonance directions. Try to depict alternative resonance structures while maintaining the lone pairs as they are. #### B. \[ \begin{aligned} \text{H}_2\text{N} & = \overset{\overset{\cdot\cdot}{\cdot}\cdot}{\text{C}}-\text{H} \\ & \| \\ & \text{C}=\text{C}-\text{H} \\ & \| \\ & \text{N}\text{H}_2 \quad \rightleftharpoons \\ \end{aligned} \] ##### Hint: Make N charged. Also, do one side at a time, but don't do both sides at the same time. \[ \begin{aligned} \text{H}_2\text{N} & \equiv \overset{+}{\text{C}}-\text{H} \\ & \| \\ & \text{C}=\text{C}-\text{H} \\ & \| \\ & \text{N}\text{H}_2 \quad \rightleftharpoons \\ \end{aligned} \] Alternatively, we can also have: \[ \begin{aligned} \text{H}_2\text{N} & = \overset{\overset{\cdot\cdot}{\cdot}\cdot}{\text{C}}-\text{H} \\ & \| \\ & \text{C}-\text{C}-\text{H} \\ & \| \\ & \text{N}\text{H}_2 \quad \\ \end{aligned} \] This problem requires adjusting molecular structures to show resonance forms. Follow the guidelines to ensure lone pairs remain unaltered,
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