General, Organic, & Biological Chemistry
3rd Edition
ISBN: 9780073511245
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Question
Chapter 4, Problem 4.46P
Interpretation Introduction
Interpretation:
The reason for the stabilization of a molecule having two resonance structures needs to be explained.
Concept introduction:
Resonance is method to describe bonding in molecules or ions that takes place by combining several contributing structures into a resonance hybrid in
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Complete the following table. The only density needed is already given. Show your
calculations in a neat and easy-to-follow manner in the space below the table. All units
should be included and significant figures should be given close attention. Be sure to notice
that the amount of material should be in millimoles rather than moles, and the theoretical
mass of the product should in milligrams rather than grams.
LOCH 3
+
H2SO4
HNO 3
O=C-OCH 3
NO2
x
H₂O
F.W.
4.0 mL 1.3 M
amount
0.50 mL
in H2SO4
mg Theoretical
Theoretical
mmoles
density
1.09
Kumada Coupling:
1. m-Diisobutylbenzene below could hypothetically be synthesized by Friedel-Crafts reaction. Write out the reaction with a
mechanism and give two reasons why you would NOT get the desired product.
Draw the reaction (NOT a mechanism) for a Kumada coupling to produce the molecule above from m-dichlorobenzene.
Calculate the theoretical yield for the reaction in question 2 using 1.5 g of p-dichlorobenzene and 3.0 mL isobutyl bromide.
What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What
other impurities are present in your product and how do you know?
Wintergreen from Aspirin:
1. In isolating the salicylic acid, why is it important to press out as much of the water as possible?
2. Write the mechanism of the esterification reaction you did.
3.
What characteristic absorption band changes would you expect in the IR spectrum on going from aspirin to salicyclic acid and
then to methyl salicylate as you did in the experiment today? Give approximate wavenumbers associated with each functional
group change.
What signals appeared/disappeared/shifted that indicate that you have your intended product and not starting material? What
other impurities are present in your product and how do you know?
Chapter 4 Solutions
General, Organic, & Biological Chemistry
Ch. 4.1 - Use electron-dot symbols to show how a hydrogen...Ch. 4.1 - Use electron-dot symbols to show how two chlorine...Ch. 4.1 - How many covalent bonds are predicted for each...Ch. 4.1 - Fill in the lone pairs on each atom to give every...Ch. 4.1 - Prob. 4.5PCh. 4.1 - Draw a Lewis structure for each covalent molecule....Ch. 4.1 - Draw a Lewis structure for dimethyl ether (C2H6O)...Ch. 4.2 - Prob. 4.8PCh. 4.2 - Prob. 4.9PCh. 4.2 - Prob. 4.10P
Ch. 4.3 - Prob. 4.11PCh. 4.3 - Prob. 4.12PCh. 4.4 - Prob. 4.13PCh. 4.4 - Draw resonance structures for each polyatomic...Ch. 4.4 - Nitrous oxide, N2O, is a sweet-smelling gas...Ch. 4.5 - Name each compound: (a) CS2; (b) SO2; (c) PCl5;...Ch. 4.5 - Prob. 4.17PCh. 4.5 - What is the shape around the indicated atom in...Ch. 4.6 - NaNH2, sodium amid, is a salt that contains a...Ch. 4.6 - Prob. 4.20PCh. 4.7 - Using the trends in the periodic table, rank the...Ch. 4.7 - Use electronegativity values to classify the...Ch. 4.7 - Prob. 4.23PCh. 4.8 - Prob. 4.24PCh. 4.9 - Prob. 4.25PCh. 4.9 - Prob. 4.26PCh. 4 - For each pair of compounds, classify the bonding...Ch. 4 - For each pair of compounds, classify the bonding...Ch. 4 - Prob. 4.29PCh. 4 - How many bonds and lone pairs are typically...Ch. 4 - Prob. 4.31PCh. 4 - Fill in the lone pairs needed to give the main...Ch. 4 - Prob. 4.33PCh. 4 - Convert the 3-D model of the general anesthetic...Ch. 4 - Draw a valid Lewis structure for each molecule. Hl...Ch. 4 - Draw a valid Lewis structure for each molecule....Ch. 4 - Prob. 4.37PCh. 4 - Prob. 4.38PCh. 4 - Draw a valid Lewis structure for...Ch. 4 - Draw a valid Lewis structure for phosgene, CCl2O ,...Ch. 4 - Draw a valid Lewis structure for each ion: (a)...Ch. 4 - Draw a valid Lewis structure for each ion: (a)...Ch. 4 - Keeping in mind that some elements violate the...Ch. 4 - Keeping in mind that some elements violate the...Ch. 4 - Prob. 4.45PCh. 4 - Prob. 4.46PCh. 4 - Prob. 4.47PCh. 4 - Prob. 4.48PCh. 4 - Prob. 4.49PCh. 4 - Label each pair of compounds are resonance...Ch. 4 - Prob. 4.51PCh. 4 - Draw three resonance structures for the nitrate...Ch. 4 - Name each covalent compound. PBr3 SO3 NCl3 P2S5Ch. 4 - Name each covalent compound. SF6 CBr4 N2O P4O10Ch. 4 - Prob. 4.55PCh. 4 - Prob. 4.56PCh. 4 - Add lone pairs where needed to give octets and...Ch. 4 - Add lone pairs where needed to give octets and...Ch. 4 - Prob. 4.59PCh. 4 - Match each compound with one of the molecular...Ch. 4 - Prob. 4.61PCh. 4 - Add lone pairs where needed to give octets and...Ch. 4 - Prob. 4.63PCh. 4 - Considering each of the given ball-and stick...Ch. 4 - Prob. 4.65PCh. 4 - Prob. 4.66PCh. 4 - Prob. 4.67PCh. 4 - Predict the bond angles around the indicated atoms...Ch. 4 - Prob. 4.69PCh. 4 - Prob. 4.70PCh. 4 - Rank the atoms in each group in order of...Ch. 4 - Prob. 4.72PCh. 4 - Prob. 4.73PCh. 4 - Using electronegativity values, classify the bond...Ch. 4 - Label the bond formed between carbon and each of...Ch. 4 - Label the bond formed between fluroine and each of...Ch. 4 - Which bond in each pair is more polar-that is, has...Ch. 4 - Which bond in each pair is more polar-that is, has...Ch. 4 - Prob. 4.79PCh. 4 - Prob. 4.80PCh. 4 - Label the polar bonds and then decide if each...Ch. 4 - Label the polar bonds and then decide if each...Ch. 4 - Prob. 4.83PCh. 4 - Explain why H2O is a polar molecule but H2S is...Ch. 4 - Convert each ball-and-stick model to a Lewis...Ch. 4 - Convert each ball-and-stick model to a Lewis...Ch. 4 - Answer the following questions about the molecule...Ch. 4 - Answer the following question about the molecule...Ch. 4 - Prob. 4.89PCh. 4 - Lactic acid gives sour milk its distinctive taste....Ch. 4 - Prob. 4.91PCh. 4 - Prob. 4.92PCh. 4 - Prob. 4.93PCh. 4 - Prob. 4.94PCh. 4 - Isobutyl cyanoacrylate is used in medical glues to...Ch. 4 - Prob. 4.96PCh. 4 - Cyclopropane is a stable compound that contains...Ch. 4 - Prob. 4.98CPCh. 4 - Prob. 4.99CPCh. 4 - Prob. 4.100CP
Knowledge Booster
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