Pushing Electrons
4th Edition
ISBN: 9781133951889
Author: Weeks, Daniel P.
Publisher: Cengage Learning
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Textbook Question
Chapter 1, Problem 30EQ
Derive Lewis structures for the compounds below.
Azobenzene
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Four 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 :
Br
[Review Topics)
[References]
Unshared, or lone, electron pairs play an important role in determining the chemical 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
H,C-
The number of unshared pairs at atom b is
CCH2
The number of unshared pairs at atom c is
e.
The number of unshared pairs at atom a is
H3C
The number of unshared pairs at atomb is
H3C
The number of unshared pairs at atom c is
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what is the complete lewis structure of acetic anhydride such that all atoms have zero formal charge?
Chapter 1 Solutions
Pushing Electrons
Ch. 1 - 1. Hydrogen is a Group I element and each...Ch. 1 - Methanol has the molecular formula CH4O. Its...Ch. 1 - 3. The skeleton of chloromethane is...Ch. 1 - 4. Methanol’s skeleton is
Connecting all bonded...Ch. 1 - 5. The structure for chloromethane is
It...Ch. 1 - Prob. 6EQCh. 1 - 7. Dimethyl ether
No. of electrons in...Ch. 1 - Methylamine (CH5N) No. of electrons in structure...Ch. 1 - Methanethiol (CH4S) No. of electrons in structure...Ch. 1 - Methylal (C3H8O2) No. of electrons in structure...
Ch. 1 - Prob. 11EQCh. 1 - Adding electrons to the skeleton by making single...Ch. 1 - This is done by removing an unshared pair from...Ch. 1 - Prob. 14EQCh. 1 - Prob. 15EQCh. 1 - Prob. 16EQCh. 1 - The skeleton of acetyl chloride is . Write the...Ch. 1 - Three constitutional isomers exist for the formula...Ch. 1 - A number of constitutional isomers exist for the...Ch. 1 - Using the method outlined above, derive the...Ch. 1 - Prob. 21EQCh. 1 - Prob. 22EQCh. 1 - Prob. 23EQCh. 1 - Prob. 24EQCh. 1 - The skeleton of benzyldimethylamine is
The...Ch. 1 - The skeleton is benzaldoxime is The number of...Ch. 1 - Prob. 27EQCh. 1 - Derive Lewis structures for the compounds below....Ch. 1 - Prob. 29EQCh. 1 - Derive Lewis structures for the compounds below....Ch. 1 - Prob. 31EQCh. 1 - Derive Lewis structures for the compounds below....Ch. 1 - The Lewis structure of acetone is Circling the...Ch. 1 - Chloromethane has the Lewis...Ch. 1 - In the Lewis structure for chloromethane, the...Ch. 1 - Prob. 36EQCh. 1 - The oxygen atom in acetone possesses ____ unshared...Ch. 1 - Nitrobenzene has the skeleton
The number of...Ch. 1 - Prob. 39EQCh. 1 - Compute and add on the formal charges I these...Ch. 1 - Prob. 41EQCh. 1 - Prob. 42EQCh. 1 - Prob. 43EQCh. 1 - Prob. 44EQCh. 1 - Prob. 45EQCh. 1 - Prob. 46EQCh. 1 - Prob. 47EQCh. 1 - Compute and add on the formal charges in these...Ch. 1 - Prob. 49EQCh. 1 - Prob. 50EQCh. 1 - The n-propyl cation can be formed from a molecule...Ch. 1 - Prob. 52EQCh. 1 - Prob. 53EQCh. 1 - Methanol, CH3OH, is a compound in which the formal...Ch. 1 - When a proton becomes bonded to diethyl ether, by...Ch. 1 - Tetrahydrofuran has the structure
When a proton...Ch. 1 - Prob. 57EQCh. 1 - Prob. 58EQCh. 1 - The structure of pyridine is
When a proton...Ch. 1 - The carbon atom owns one electron from each of ...Ch. 1 - The n-butyl anion can be formed from When the CLi...Ch. 1 - The isobutyl anion can be formed from When the CNa...Ch. 1 - Prob. 63EQCh. 1 - Ethanol, , is a compound in which the formal...Ch. 1 - The loss of a proton attached to the oxygen atom...Ch. 1 - A very strong base can remove a proton from...Ch. 1 - Prob. 67EQCh. 1 - Prob. 68EQCh. 1 - Prob. 69EQCh. 1 - The homolysis of the OO bond in diacetyl peroxide...Ch. 1 - Prob. 71EQCh. 1 - Prob. 72EQCh. 1 - Prob. 73EQCh. 1 - Prob. 74EQCh. 1 - Prob. 75EQCh. 1 - Heterolytic cleavage of the CO bond to yield a...Ch. 1 - Prob. 77EQCh. 1 - Prob. 78EQCh. 1 - Prob. 79EQCh. 1 - Prob. 80EQ
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- Give the organic family the compound shown here belongs to. NH₂ C-C-C-C-C-C-C The organic family the molecule shown above belongs to is a(n)arrow_forward[Review Topics] [References] Unshared, or lone, electron pairs play an important role in determining the chemical 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. H3C -C=N=O a H₂C-C=N a b C Submit Answer C The number of unshared pairs at atom a is The number of unshared pairs at atom b is The number of unshared pairs at atom c is The number of unshared pairs at atom a is The number of unshared pairs at atom b is The number of unshared pairs at atom c is Retry Entire Group 1 more group attempt remaining Varrow_forwardUnshared, 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
- Provide a systematic name for each of the following compoundsarrow_forwardWhat will be the formula and electron dot structure of cyclopentane?arrow_forwardYou will not find “hydroxide” in the stockroom, but you will find sodium hydroxide (NaOH) andpotassium hydroxide (KOH). Lithium hydroxide (LiOH) is expensive and used in spacecraft airfilters since hydroxide reacts with carbon dioxide, and lithium is lighter than sodium or potassium.Cesium and francium hydroxides are very expensive and little used. Is this information consistentwith your answer to the previous question?arrow_forward
- Ethanol, , 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_forwardExperimentally, the shape around the highlighted nitrogens is found to be trigonal planar rather than trigonal pyramidal predicted by the Lewis structure above. Sketch a resonance structure that would account for trigonal planar geometry about the highlighted nitrogens in uracil. Add formal charges to the four atoms that have non-zero formal charges. LA O--arrow_forwardThe compound whose structure is shown here is acetyl acetone. It exists in two forms:the enol form and the keto form The molecule reacts with OH–to form an anion, [CH3COCHCOCH3] (often abbreviatedacac–for acetylacetonate ion). One or the most interesting aspects of this anion is thatone or more of them can react with transition metal cations to give stable, highlycolored compounds (a) Are the keto and enol forms of acetylacetone resonance forms? Explain youranswer.(b) What is the hybridization or each atom (except H) in the enol form? What changesin hybridization occur when it is transformed into the keto form?(c) What are the electron-pair geometry and molecular geometry around each C atomin the keto and enol forms? What changes in geometry occur when the keto formchanges to the enol form?(d) Draw three possible resonance structures for the acac–ion.(e) Is cis-trans isomerism possible in either the enol or the keto form of acetylacetone?(f) Is the enol form of acetylacetone polar?…arrow_forward
- 1. Draw Lewis structures for the following compounds. Remember to enclose ions in square brackets. On your answer sheet, state the number of valence electrons in each compound. (a) Na₂S (b) (CH3)₂S (c) KOCI List the most important (etrongnet) inarrow_forwardPlease explain. I’m very confused on what to do. I know it has to deal with arrowsarrow_forwardWrite an equation to show the reaction between ethanol, C2H5OH and methyllithium, CH3 Draw all non-bonding electrons and show electron flow with curved arrows.arrow_forward
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