Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

1. A Review of General Chemistry

Molecular Geometry

Organic Chemistry

1. A Review of General Chemistry

Molecular Geometry

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Problem 52c

Textbook Question

For each of the following compounds and ions,
1. Draw a Lewis structure.
2. Show the kinds of orbitals that overlap to form each bond.
3. Give approximate bond angles around each atom except hydrogen.
c. CH₂=N–CH₃

Verified step by step guidance

Step 1: Draw the Lewis structure for CH2=NCH3. Start by counting the total number of valence electrons. Carbon has 4 valence electrons, nitrogen has 5, and hydrogen has 1. The total is 18 valence electrons.

Step 2: Arrange the atoms with carbon as the central atom for the CH2 group and nitrogen as the central atom for the NCH3 group. Connect the atoms with single bonds initially, and then adjust to satisfy the octet rule, forming a double bond between carbon and nitrogen.

Step 3: Identify the types of orbitals involved in bonding. The C-H bonds are formed by the overlap of sp3 hybrid orbitals from carbon with the s orbitals of hydrogen. The C=N double bond involves sp2 hybrid orbitals from carbon and nitrogen, with one sigma bond and one pi bond.

Step 4: Determine the hybridization of each atom. The carbon in CH2 is sp2 hybridized, the nitrogen is sp2 hybridized, and the carbon in CH3 is sp3 hybridized.

Step 5: Estimate the bond angles. Around the sp2 hybridized carbon and nitrogen, the bond angles are approximately 120 degrees. Around the sp3 hybridized carbon in CH3, the bond angles are approximately 109.5 degrees.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Lewis Structure

A Lewis structure is a diagram that represents the valence electrons of atoms within a molecule. It shows how atoms are bonded together and the lone pairs of electrons. For CH2=NCH3, the structure involves drawing the carbon-nitrogen double bond and ensuring the correct placement of hydrogen atoms and lone pairs on nitrogen.

Orbital Overlap

Orbital overlap refers to the interaction between atomic orbitals that leads to bond formation. In CH2=NCH3, the carbon-nitrogen double bond involves sp2 hybridized orbitals overlapping with a p orbital from nitrogen, while the single bonds between carbon and hydrogen involve sp3 hybridized orbitals overlapping with s orbitals from hydrogen.

Bond Angles

Bond angles are the angles between adjacent bonds at an atom. They are determined by the hybridization and geometry of the molecule. In CH2=NCH3, the bond angles around the sp2 hybridized carbon are approximately 120 degrees, while the angles around the sp3 hybridized carbon in CH3 are approximately 109.5 degrees.

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Describe the orbitals used in bonding and the bond angles in the following compounds:

e. BF₃

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a. the methyl cation.

b. the methyl radical.

c. the methyl anion.

Textbook Question

Predict the approximate bond angles for the following:

c. the C—C—N bond angle in CH₃C≡N

d. the C—C—N bond angle in CH₃CH₂NH₂

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Circle the coplanar atoms in the following structure:

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(d) CO₃^2-

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(b) the C—N—C bond angle in a secondary amine

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Describe the orbitals used in bonding and the bond angles in the following compounds:

a. CH₃O^-

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