Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 1, Problem 71DSP
Amide Lewis Structural Formulas
Lewis formulas are the major means by which structural information is communicated in
Two or more Lewis formulas, differing only in the placement of electrons, can often be written for a single compound. In such cases the separate structures represented by the Lewis formulas are said to be in resonance, and the true electron distribution is a hybrid of the electron distributions of the contributing structures.
The amide function is an important structural unit in peptides and proteins. Formamide, represented by the Lewis structure shown, is the simplest amide. It is a planar molecule with a dipole moment of
D. Lewis structures I–IV represent species that bear some relationship to the Lewis structure for formamide.
According to VSEPR, which Lewis formula has a pyramidal
arrangement of bonds to nitrogen?
I
II
III
IV
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
1) Choose a period from the Periodic Table.
2) Identify the period by its number and indicate the first atom and the last one, indicating to which group each one corresponds.
3) Write the electronic configuration of each representative element of the chosen period.
4) Determine the valence electrons of each of these elements.
5) Compare the number of valence electrons of the first and last element of the period.
6) Compare the electronic configurations. Point out similarities and differences in a synthesis of what was observed.
For each of the following compounds, 1. draw the Lewis structure.
2. show how the bond dipole moments (and those of any nonbonding pairs of electrons) contribute to the molecular dipole moment.
3. estimate whether the compound will have a large, small, or zero dipole moment.
Explain the inductive effect in organic chemistry by using the example of diketones.
Chapter 1 Solutions
Organic Chemistry - Standalone book
Ch. 1.1 - How many electrons does carbon have? How many are...Ch. 1.1 - Referring to the periodic table as needed, write...Ch. 1.2 - Species that have the same number of electrons are...Ch. 1.2 - Which of the following ions possess a noble gas...Ch. 1.2 - Prob. 5PCh. 1.3 - Prob. 6PCh. 1.3 - Problem 1.7 All of the hydrogens are bonded to...Ch. 1.4 - Problem 1.8 In which of the compounds...Ch. 1.4 - Indicate the direction of the dipole for the...Ch. 1.5 - Prob. 10P
Ch. 1.5 - The following inorganic species will be...Ch. 1.5 - Prob. 12PCh. 1.6 - Prob. 13PCh. 1.6 - Problem 1.14 Nitrosomethane and formaldoxime both...Ch. 1.6 - Prob. 15PCh. 1.7 - All of the bonds in the carbonate ion (CO32-) are...Ch. 1.7 - Prob. 17PCh. 1.8 - Prob. 18PCh. 1.8 - Prob. 19PCh. 1.9 - Sodium borohydride, NaBH4, has an ionic bond...Ch. 1.9 - Prob. 21PCh. 1.10 - Which of the following compounds would you expect...Ch. 1.11 - Using the curved arrow to guide your reasoning,...Ch. 1.11 - Prob. 24PCh. 1.11 - Prob. 25PCh. 1.12 - Prob. 26PCh. 1.12 - Prob. 27PCh. 1.12 - Prob. 28PCh. 1.12 - Prob. 29PCh. 1.12 - Prob. 30PCh. 1.13 - Which is the stronger acid, H2O or H2S? Which is...Ch. 1.13 - Prob. 32PCh. 1.13 - Prob. 33PCh. 1.13 - Hypochlorous and hypobromous acid (HOClandHOBr)...Ch. 1.13 - Prob. 35PCh. 1.13 - Prob. 36PCh. 1.14 - What is the equilibrium constant for the following...Ch. 1.14 - Prob. 38PCh. 1.14 - Prob. 39PCh. 1.15 - Write an equation for the Lewis acid/Lewis base...Ch. 1 - Write a Lewis formula for each of the following...Ch. 1 - Prob. 42PCh. 1 - Write structural formulas for all the...Ch. 1 - Prob. 44PCh. 1 - Expand the following structural representations so...Ch. 1 - Each of the following species will be encountered...Ch. 1 - Consider Lewis formulas A, B, and C: H2 C -NN:...Ch. 1 - Prob. 48PCh. 1 - Prob. 49PCh. 1 - Prob. 50PCh. 1 - Prob. 51PCh. 1 - Prob. 52PCh. 1 - Prob. 53PCh. 1 - Prob. 54PCh. 1 - Which compound in each of the following pairs...Ch. 1 - With a pKa of 11.6, hydrogen peroxide is a...Ch. 1 - The structure of montelukast, an antiasthma drug,...Ch. 1 - One acid has a pKa of 2, the other has a pKa of 8....Ch. 1 - Calculate Ka for each of the following acids,...Ch. 1 - Rank the following in order of decreasing acidity....Ch. 1 - Rank the following in order of decreasing...Ch. 1 - Consider 1.0 M aqueous solutions of each of the...Ch. 1 - Prob. 63PCh. 1 - Prob. 64PCh. 1 - Prob. 65PCh. 1 - Prob. 66PCh. 1 - Prob. 67PCh. 1 - Prob. 68PCh. 1 - Amide Lewis Structural Formulas Lewis formulas are...Ch. 1 - Amide Lewis Structural Formulas Lewis formulas are...Ch. 1 - Amide Lewis Structural Formulas Lewis formulas are...Ch. 1 - Prob. 72DSPCh. 1 - Amide Lewis Structural Formulas Lewis formulas are...Ch. 1 - Amide Lewis Structural Formulas Lewis formulas are...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Unshared, or lone, electron pairs play an important role in determining the chermical and physical properties of organic compounds. Thus, it is important to know which atoms carry unshared pairs. Use the structural formulas below to determine the number of unshared pairs at each designated atom. Be sure your answers are consistent with the formal charges on the formulas. The number of unshared pairs at atom a is The number of unshared pairs at atom b is HyC CH The number of unshared pairs at atom e is The number of unshared pairs at atom a is The number of unshared pairs at atom b is HC CH The number of unshared pairs at atom e isarrow_forward[Review Topics] [References] Use the References to access important values if needed for this question. Use the following Lewis diagram for propanoic acid to answer the questions: H H :0: Remember that geometry refers to the geometry defined by the atoms, not the electron pairs. The geometry about atom C, is trigonal planar The ideal value of the C-C-C angle at atom C2 is 180 degrees. The geometry about atom C3 is bent An error has been detected in your answer. Check for typos, miscalculations etc. before submitting your answer. Submit Answer Retry Entire Group 8 more group attempts remaining Previous Nextarrow_forwardUsing all the information provided come up with the structure of the compoundarrow_forward
- Arrange the following acids in order of decreasing acidity. Justify your choices, making sure to use the space below to analyze each compound and determine the factor(s) contributing to the acidity. Lone pairs and formal charges are not provided. Include resonance structures where appropriate; do not forget to draw lone pairs and formal charges as necessary.arrow_forwardEthanol, , is a compound in which the formal charge on all the atoms is zero. Under certain conditions the bond can be broken so that both electrons remain with the oxygen atom. The products are In this structure the oxygen owns one electron from shared pair and two electrons from each of unshared pairs. The total number of electrons belonging to oxygen is Oxygen is a Group element. The formal charge on the oxygen atom is . The correct Lewis structure for the ethoxide ion is Note that the other fragment, the proton, leaves with a formal charge of +1.arrow_forwardFour major contributing resonance structures are possible for the given cation, which is the intermediate o complex of an electrophilic aromatic substitution involving phenol and bromine. Two structures are given but are incomplete. Complete the given structures by adding nonbonding electrons and formal charges. Draw the remaining structures (in any order), including nonbonding electrons and formal charges. Complete structure A. Complete structure B. : 0 H :0- Br : Brarrow_forward
- Using the concept of aromaticity and resonance, determine which of the following compounds has the largest dipole moment. Explain your selectionarrow_forwardCompare with explanation the acidity of the following pairs of compounds. (Note: You must draw the appropriate resonance structures to support your answers.) (c) (i) .COOH .COOH H3COarrow_forwardGive the molecular formula, the line bond structural formula, the condensed structural formula, and the skeletal formula for octane. 4. Molecular formula: Line bond structural formula:arrow_forward
- Two useful organic compounds that contain Cl atoms are vinyl chloride (CH2 = CHCI) and chloroethane (CH;CH;CI). Vinyl chloride is the starting material used to prepare poly (vinyl chloride), a plastic used in insulation, pipes, and bottles. Chloroethane (ethyl chloride) is a local anesthetic. Why is the C – Cl bond of | vinyl chloride stronger than the C – Cl bond in chloroethane.arrow_forwardnaming a chemical compound. I'm currently learning how to name alkanes and alkyl halides. Im confused about the compound ethanal, or acetaldehyde. The second carbon has a double bond on its hydrogen, so I'm wondering why the infix is "an" instead of "en". Frpm the table of infixes, it says "an" is for single bonds. Can someone help me understandarrow_forwardOrganic chemistry: please explain this textbook question. Predict the structure of the unknown compound using the provided information. All spectra provided for each unknown must be utilized to arrive at your answer. Please it should be clear how each spectra was used to help determine the unknown. Please annotate all spectra. Please provide the HDI and chemical formula and the final structure in bond line notation.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Principles of Modern ChemistryChemistryISBN:9781305079113Author:David W. Oxtoby, H. Pat Gillis, Laurie J. ButlerPublisher:Cengage Learning
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Introductory Chemistry: An Active Learning Approa...ChemistryISBN:9781305079250Author:Mark S. Cracolice, Ed PetersPublisher:Cengage Learning
Chemistry: Matter and ChangeChemistryISBN:9780078746376Author:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl WistromPublisher:Glencoe/McGraw-Hill School Pub Co
Principles of Modern Chemistry
Chemistry
ISBN:9781305079113
Author:David W. Oxtoby, H. Pat Gillis, Laurie J. Butler
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Introductory Chemistry: An Active Learning Approa...
Chemistry
ISBN:9781305079250
Author:Mark S. Cracolice, Ed Peters
Publisher:Cengage Learning
Chemistry: Matter and Change
Chemistry
ISBN:9780078746376
Author:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl Wistrom
Publisher:Glencoe/McGraw-Hill School Pub Co
General Chemistry | Acids & Bases; Author: Ninja Nerd;https://www.youtube.com/watch?v=AOr_5tbgfQ0;License: Standard YouTube License, CC-BY