Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 1.9, Problem CQ
Interpretation Introduction
Interpretation:
The reasonable contributing structure for the amide bond of the molecule has to be shown.
Concept introduction:
Resonance: The delocalization of electrons which is characterized as several structural changes.
Amide:
A carbon atom is double-bonded to an oxygen atom
If the carbonyl carbon is attached with nitrogen is called as amide.
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Complete Table 3 (Remember that the values pertain to the Central atoms only. In this table, you will have more than one central atom so report more than one value, ie. 3 / 3)
Table 3 Molecules with Multiple Central Atoms
Molecule
C2H4
H2O2.
CH3OH.
CH3NH2
Number of Bond Pairs
/
/
/
/
Number of Lone Pairs
/
/
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Number of Electron Domains
/
/
/
/
Molecular Geometry (Shape)
/
/
/
/
Bond Angle
/
/
/
/
Polar or Non-Polar
Nonpolar
Polar
Polar
Polar
2. Answer parts a-e using the skeletal structure of the molecule shown below.
NE
#
NC=N;
+
NÁ
a. Add all implied hydrogen atoms to the skeletal structure.
b. How many tetrahedral carbons are in the molecule? What hybridization do tetrahedral
carbon atoms have?
c. Consider the bond marked by *. Based on what you know about electronegativity trends,
which atom in the bond is more electron rich? Draw a dipole arrow pointing toward the
more electron rich atom.
d. Label each N atom with its hybridization (sp, sp², or sp³). Based on the hybridization that
you assigned, what atomic orbitals does each N atom possess? (Hint: Each atom should
always have 4 atomic orbitals.)
NA atomic orbitals NB atomic orbitals Ne atomic orbitals ND atomic orbitals
e. Consider the lone pair on each nitrogen atoms. What atomic or hybridized atomic orbital
holds each lone pair (sp, sp², sp³, s, or p)?
Lone pair on N₁ held by Lone pair on NB held by Lone pair on ND held by
5. NO₂-¹
Total # of Valence Electrons:
Lewis Structure (show all resonance structures if applicable)
3-D Model Sketch
Any polar bonds in the molecule? Yes No
Molecular Shape:
Molecular Polarity:
Any polar bonds in the molecule? Yes No
6. H30*¹ — use a yellow ball for oxygen (not red) when constructing this model
Total # of Valence Electrons:
3-D Model Sketch
Lewis Structure (show all resonance structures if applicable)
Molecular Shape:
Molecular Polarity:
Polar
Polar
Bond Angles
Non-Polar
Bond Angles
Non-Polar
Chapter 1 Solutions
Organic Chemistry
Ch. 1.1 - Prob. 1.1PCh. 1.2 - Prob. 1.2PCh. 1.2 - Judging from their relative positions in the...Ch. 1.2 - Classify each bond as nonpolar covalent or polar...Ch. 1.2 - Using the symbols and +, indicate the direction...Ch. 1.2 - Draw Lewis structures showing all valence...Ch. 1.2 - Draw Lewis structures for these ions and show...Ch. 1.3 - Draw Lewis structures and condensed structural...Ch. 1.3 - Prob. 1.9PCh. 1.3 - Prob. 1.10P
Ch. 1.3 - Prob. 1.11PCh. 1.3 - Prob. 1.12PCh. 1.4 - Predict all bond angles for these molecules. (a)...Ch. 1.5 - The geometry of carbon in diamond is tetrahedral,...Ch. 1.5 - Because of their spherical shape, C60 molecules...Ch. 1.5 - What best describes the CCC bond angles in C60? 1....Ch. 1.5 - Prob. 1.14PCh. 1.7 - Describe the bonding in these molecules in terms...Ch. 1.8 - Prob. 1.16PCh. 1.8 - Prob. 1.17PCh. 1.8 - Prob. 1.18PCh. 1.9 - Draw three contributing structures of the...Ch. 1.9 - What is the hybridization state of the circled...Ch. 1.9 - The molecule shown on the right in the example in...Ch. 1.9 - Prob. CQCh. 1.9 - The following structure is called imidazolium....Ch. 1 - Write the ground-state electron configuration for...Ch. 1 - Identify the atom that has each ground-state...Ch. 1 - Define valence shell and valence electron.Ch. 1 - How many electrons are in the valence shell of...Ch. 1 - Prob. 1.24PCh. 1 - Prob. 1.25PCh. 1 - Prob. 1.26PCh. 1 - Write Lewis structures for these compounds. Show...Ch. 1 - Write Lewis structures for these ions. Show all...Ch. 1 - Prob. 1.29PCh. 1 - Some of these structural formulas are incorrect...Ch. 1 - Following the rule that each atom of carbon,...Ch. 1 - Following are several Lewis structures showing all...Ch. 1 - Which statements are true about electronegativity?...Ch. 1 - Why does fluorine, the element in the upper right...Ch. 1 - Arrange the single covalent bonds within each set...Ch. 1 - Using the values of electronegativity given in...Ch. 1 - Prob. 1.37PCh. 1 - Use VSEPR to predict bond angles about each...Ch. 1 - Use VSEPR to predict bond angles about each atom...Ch. 1 - Use VSEPR to predict the geometry of these ions....Ch. 1 - Prob. 1.41PCh. 1 - Prob. 1.42PCh. 1 - What is the meaning of the term tertiary (3) when...Ch. 1 - What is the meaning of the term tertiary (3) when...Ch. 1 - Draw structural formulas for (a) The four primary...Ch. 1 - Draw structural formulas for the three tertiary...Ch. 1 - Prob. 1.47PCh. 1 - Identify the functional groups in each compound.Ch. 1 - Draw a three-dimensional representation for each...Ch. 1 - Tetrafluoroethylene, C2F4, is the starting...Ch. 1 - Which statements are true about resonance...Ch. 1 - Prob. 1.52PCh. 1 - Prob. 1.53PCh. 1 - Prob. 1.54PCh. 1 - Are the structures in each set valid contributing...Ch. 1 - State the orbital hybridization of each...Ch. 1 - Describe each highlighted bond in terms of the...Ch. 1 - Following is a structural formula of the...Ch. 1 - Draw a Lewis structure for methyl isocyanate,...Ch. 1 - What is the hybridization of the highlighted atoms...Ch. 1 - Using cartoon representations, draw a molecular...Ch. 1 - In what kind of orbitals do the lone-pair...Ch. 1 - Draw the delocalized molecular orbitals for the...Ch. 1 - Prob. 1.64APCh. 1 - Each compound contains both ions and covalent...Ch. 1 - Predict whether the carbon-metal bond in these...Ch. 1 - Prob. 1.67APCh. 1 - Phosphorus is immediately under nitrogen in the...Ch. 1 - Draw a Lewis structure for the azide ion, N3. (The...Ch. 1 - Cyanic acid, HOCN, and isocyanic acid, HNCO,...Ch. 1 - In Chapter 6, we study a group of organic cations...Ch. 1 - Many reactions involve a change in hybridization...Ch. 1 - Following is a structural formula of benzene,...Ch. 1 - Following are three contributing structures for...Ch. 1 - (a) Draw a Lewis structure for the ozone molecule,...Ch. 1 - The following two compounds are isomers; that is,...Ch. 1 - In future chapters, we will encounter...Ch. 1 - Prob. 1.78AP
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