Organic Chemistry — Bonding and Structure: Interpret Chemical Structure Line Drawing

Question

How many carbons are in the following drawing? How many hydrogens?

A line structure drawing showing a single line connecting to two lines, one of which is a double line that connects to another single line.

 

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5 carbons; 10 hydrogens

Refer to Section 7.2: Drawing Chemical Structures (1).

Strategy Map

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Table 1: Strategy Map
Strategy Map Steps
1. Identify the carbons in the line drawing for the molecule.

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In a line structure, carbon atoms are found at the end of each line as well as at each corner.

2. Add hydrogen atoms to the carbons until each carbon has 4 bonds.

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This will satisfy the octet rule.

3. Count the carbon atoms and the hydrogen atoms in the molecule.

Solution

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A CH3 group connected to a carbon with a CH3 off it and a double bond to another carbon, which is then bonded to another CH3 group.The full Lewis Structure shows that this molecule has 5 carbon atoms and 10 hydrogen atoms.

Guided Solution

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The guided solution below will give you the reasoning for each step to get your answer, with reminders and hints.

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Table 2: Guided Solution
Guided Solution Ideas
This question is a theory problem that requires you to identify all implied carbons and hydrogens in a line structure.

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Refer to Section 7.2: Drawing Chemical Structures (1).

What do the lines represent? Where are the implied carbons and hydrogens?

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Recall that in a line structure, carbon atoms are found at the end of each line as well as at each corner. Hydrogen atoms surround the carbons to satisfy the octet rule.

Draw the structure of the molecule showing all carbon and hydrogen atoms. Remember to fulfill the octet rule.

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Recall your steps for drawing Lewis Structures.

Refer to Section 4.4: Lewis Symbols and Structures (2).

Table 3: Complete Solution
Complete Solution
In a line structure, carbons are at either end of each line as well as in every corner. A double line shows the double bond.

Start by writing in the carbon atoms and their connectivity based on the line diagram.

Show/Hide Structure!

A chain of four carbons with the second carbon having a single bond to one terminal carbon and a double bond to the third carbon.

Then, add hydrogen atoms to each C atom until each C has 4 bonds.

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A CH3 group connected to a carbon with a CH3 off it and a double bond to another carbon, which is then bonded to another CH3 group.

Count the carbon and hydrogen atoms shown in the structure.

Answer: In this molecule, there are 5 carbon atoms and 10 hydrogen atoms.

Check Your Work

Summary of what we would expect based on the related chemistry theory

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Counting valence electrons, there are 4 for each C and 1 for each H, making a total of 30 valence electrons. The Lewis Structure shows 30 valence electrons and satisfies the octet rule.

Does your answer make chemical sense?

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The full structure represents the Lewis Structure for this molecule. There are 5 carbon atoms, which matches the line structure given in the question, and 10 hydrogen atoms, which satisfies the octet rule for each carbon.

There are many ways to draw molecules. A line structure gives us the ability to quickly create carbon-hydrogen structures. By convention, we know that each line represents the carbon-to-carbon bond and that all hydrogen atoms are “hidden.”

Refer to Section 4.4: Lewis Symbols and Structures (2).

PASS Attribution

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References

1. Farmer, S.; Kennepohl, D.; Cunningham, K.; Soderburg, T.; Reusch, W. 7.2: Drawing Chemical Structures. In CHEM 1500: Chemical Bonding and Organic Chemistry; LibreTexts, 2022. https://chem.libretexts.org/Courses/Thompson_Rivers_University/CHEM_1500%3A_Chemical_Bonding_and_Organic_Chemistry/07%3A_Organic_Chemistry_I_-_Bonding_and_Structure/7.02%3A_Drawing_Chemical_Structures.

2. Elles, L. S. 4.4 Lewis Symbol and Structures. In CHEM 130 and 135: General Chemistry I and II (Sharpe Elles); LibreTexts, 2023. https://chem.libretexts.org/Courses/University_of_Kansas/CHEM_130%3A_General_Chemistry_I_(Sharpe_Elles)/04%3A_Chemical_Bonding_and_Molecular_Geometry/4.04%3A_Lewis_Symbols_and_Structures#:~:text=We%20use%20Lewis%20symbols%20to,period%20of%20the%20periodic%20table.

3. Blackstock, L.; Brewer, S.; Jensen, A. PASS Chemistry Book CHEM 1500; LibreTexts, 2023. https://chem.libretexts.org/Courses/Thompson_Rivers_University/PASS_Chemistry_Book_CHEM_1500.

4. Blackstock, L.; Brewer, S.; Jensen, A. 7.2: Question 7.2 PASS – Interpret Chemical Structure Line Drawing. In PASS Chemistry Book CHEM 1500; LibreTexts, 2023. https://chem.libretexts.org/Courses/Thompson_Rivers_University/PASS_Chemistry_Book_CHEM_1500/07%3A_Organic_Chemistry_I_-_Bonding_and_Structure/7.02%3A_Question_7.2_PASS_-_interpret_chemical_structure_line_drawing.

5. Farmer, S.; Kennepohl, D.; Cunningham, K.; Soderburg, T.; Reusch, W. 1.12: Drawing Chemical Structures . In Organic Chemistry (Morsch et al.); LibreTexts, 2023. https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(Morsch_et_al.)/01%3A_Structure_and_Bonding/1.12%3A_Drawing_Chemical_Structures.

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