Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 1.7, Problem 9P
Convert the following molecular model of hexane, a component of gasoline, into a line-bond structure (gray = C, ivory = H).
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(a) Write a condensed formula for the
VSEPR diagram given on the right.
There may be more than one answer.
H
H.
I
HH
HH
HH
H
(b) Does the species have resonance structures that do not violate the octet rule? Explain.
3. (a) Draw a resonance structure for Molecule 1 in Box B, which satisfies the octet for all non-
hydrogen atoms. Hint you may want to use curved arrows to move electrons over the skeleton of
Molecule 3 to help you find the resonance structure.
H
H
H
H
Molecule 1
H
H
3. (b) Fill in the table below for Molecule 1
Box B: Resonance Structure of Molecule 1
VSEPR electron pair
geometry around
atom
Molecular geometry
Approximate bond
or shape around atom angles around atom
N atom
CH3 C atom
CH C atoms
3. (c) Given the information that resonating electrons are delocalized and so are not used to
determine VSEPR geometry, how will the table you filled in for 3.(b) change?
The following organic compound, or a derivative thereof, is important in certain metabolic processes.
Complete the Lewis diagram before answering the following questions.
How many pi bonds are there in a molecule of isocitric acid? How many sigma bonds are there in a molecule of isocitric acid? How many valence electrons are there in a molecule of isocitric acid?
Chapter 1 Solutions
Organic Chemistry
Ch. 1.3 - Give the ground-state electron configuration for...Ch. 1.3 - How many electrons does each of the following...Ch. 1.4 - Prob. 3PCh. 1.4 - Convert the following representation of ethane,...Ch. 1.4 - What are likely formulas for the following...Ch. 1.4 - Prob. 6PCh. 1.4 - Prob. 7PCh. 1.7 - Draw a line-bond structure for propane, CH3CH2CH3....Ch. 1.7 - Convert the following molecular model of hexane, a...Ch. 1.8 - Draw a line-bond structure for propene, CH3CH=CH2....
Ch. 1.8 - Draw a line-bond structure for 1, 3-butadiene,...Ch. 1.8 - Following is a molecular model of aspirin...Ch. 1.9 - Draw a line-bond structure for propyne, CH3C≡CH....Ch. 1.10 - Prob. 14PCh. 1.12 - Prob. 15PCh. 1.12 - Prob. 16PCh. 1.12 - The following molecular model is a representation...Ch. 1.SE - Convert each of the following molecular models...Ch. 1.SE - The following model is a representation of citric...Ch. 1.SE - The following model is a representation of...Ch. 1.SE - The following model is a representation of...Ch. 1.SE - How many valence electrons does each of the...Ch. 1.SE - Give the ground-state electron configuration for...Ch. 1.SE - Prob. 24APCh. 1.SE - Prob. 25APCh. 1.SE - Draw an electron-dot structure for acetonitrile,...Ch. 1.SE - Draw a line-bond structure for vinyl chloride,...Ch. 1.SE - Fill in any nonbonding valence electrons that are...Ch. 1.SE - Convert the following line-bond structures into...Ch. 1.SE - Convert the following molecular formulas into...Ch. 1.SE - Prob. 31APCh. 1.SE - Oxaloacetic acid, an important intermediate in...Ch. 1.SE - Prob. 33APCh. 1.SE - Potassium methoxide, KOCH3, contains both covalent...Ch. 1.SE - What is the hybridization of each carbon atom in...Ch. 1.SE - Prob. 36APCh. 1.SE - Prob. 37APCh. 1.SE - What bond angles do you expect for each of the...Ch. 1.SE - Propose structures for molecules that meet the...Ch. 1.SE - What kind of hybridization do you expect for each...Ch. 1.SE - Pyridoxal phosphate, a close relative of vitamin...Ch. 1.SE - Prob. 42APCh. 1.SE - Prob. 43APCh. 1.SE - Quetiapine, marketed as Seroquel, is a heavily...Ch. 1.SE - Tell the number of hydrogens bonded to each carbon...Ch. 1.SE - Why do you suppose no one has ever been able to...Ch. 1.SE - Allene, H2C=C=CH2, is somewhat unusual in that it...Ch. 1.SE - Allene (see Problem 1-47) is structurally related...Ch. 1.SE - Complete the electron-dot structure of caffeine,...Ch. 1.SE - Most stable organic species have tetravalent...Ch. 1.SE - A carbanion is a species that contains a...Ch. 1.SE - Divalent carbon species called carbenes are...Ch. 1.SE - There are two different substances with the...Ch. 1.SE - There are two different substances with the...Ch. 1.SE - There are two different substances with the...Ch. 1.SE - Prob. 56APCh. 1.SE - Among the most common over-the-counter drugs you...
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- When drawing the Lewis structure of the HCC13 molecule, the structure should represent a total of 26 valence electrons. What is the best description of the complete Lewis structure of the molecule? Select one: AH atom should be in the center with single bonds to each Cl atom and a double bond to the C atom. A Cl atom should be in the center with a single bond to the C atom and a single bond to the H atom. AC atom should be in the center with a double bond to the H atom and double bonds to each Cl atom. AC atom should be in the center with single bonds to each Cl atom and a single bond to the H atom.arrow_forwardIdentify the type of bond (ionic or covalent) in the following compounds. (a) ammonia (NH3), (b) salt (Nacl), (c) carbon tetrachloride (CCI4), (d) hydrogen peroxide (H202), (e) ozone (03), (f) ethylene (CH2=CH2) (g) water (H20), (h) magnesium oxide (MgO), (i) diamond (C).arrow_forwardHow do you know when to draw a solid wedge vs a dashed wedge when drawing 3D bond-line structures? I know that solid-wedge means the atom is pointing towards you and dashed wedge means it's in the back, but how do you know which atoms are in the front as opposed to the back? How can you tell what the configuration will look like in space just by looking at the lewis structure or name?arrow_forward
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