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Ch.17 Carboxylic Acids and Their Derivatives
McMurry - Fundamentals of GOB 8th Edition
McMurry8th EditionFundamentals of GOBISBN: 9780134015187Not the one you use?Change textbook
Chapter 17, Problem 35a(ii)

Draw the structures of the following compounds and use dashed lines to indicate where they form hydrogen bonds to other molecules of the same kind: (ii) methyl formate

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Identify the molecular structure of methyl formate. Methyl formate is an ester with the formula CH₃OCHO. It consists of a methyl group (CH₃) attached to an oxygen atom, which is connected to a carbonyl group (C=O) and a hydrogen atom.
Draw the Lewis structure of methyl formate. Start by placing the carbonyl group (C=O) in the center, with the oxygen atom bonded to the methyl group (CH₃) on one side and a hydrogen atom on the other side.
Determine the potential hydrogen bond donors and acceptors in the molecule. The oxygen atom in the carbonyl group (C=O) and the oxygen atom bonded to the methyl group (CH₃) can act as hydrogen bond acceptors due to their lone pairs of electrons. However, methyl formate does not have a hydrogen atom directly bonded to an electronegative atom (like O, N, or F), so it cannot act as a hydrogen bond donor.
Use dashed lines to indicate hydrogen bonds between molecules. Since the oxygen atoms in methyl formate can accept hydrogen bonds, draw dashed lines from the lone pairs on these oxygen atoms to hydrogen atoms in other molecules that are capable of donating hydrogen bonds (e.g., water or other hydrogen bond donors).
Label the hydrogen bonds clearly in your drawing. Indicate the lone pairs on the oxygen atoms and show the interaction between the lone pairs and the hydrogen atoms of other molecules. Ensure the dashed lines represent the non-covalent hydrogen bonding interactions.

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Key Concepts

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

Hydrogen Bonding

Hydrogen bonding is a type of weak chemical bond that occurs when a hydrogen atom covalently bonded to a highly electronegative atom, such as oxygen or nitrogen, experiences an attraction to another electronegative atom. This interaction is crucial in determining the physical properties of compounds, such as boiling and melting points, and is significant in biological systems, influencing the structure of proteins and nucleic acids.
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Methyl Formate Structure

Methyl formate is an ester with the chemical formula HCOOCH3. It consists of a formate group (HCOO) bonded to a methyl group (CH3). Understanding its molecular structure is essential for visualizing how it interacts with other molecules, particularly in the context of hydrogen bonding, where the oxygen atom in the formate group can act as a hydrogen bond acceptor.
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Dashed Lines in Molecular Diagrams

In molecular diagrams, dashed lines are commonly used to represent hydrogen bonds, indicating a non-covalent interaction between molecules. This notation helps to visualize the spatial arrangement and connectivity of molecules, particularly in complex structures where hydrogen bonding plays a significant role in stability and reactivity.
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