Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 1, Problem 1.40SP
For each of the following structures,
- 1. Draw a Lewis structure; fill in any nonbonding electrons.
- 2. Calculate the formal charge on each atom other than hydrogen.
- a. CH3NO (nitrosomethane)
- b. (CH3)3NO (trlmothylamino oxide)
- c. [N3]− (azide ion)
- d. [(CH3)3O]+
- e. CH3NC
- f. (CH3)4NBr
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Draw possible resonance structures for the following, including curved arrows showing the
movement of electrons and any relevant formal charges.
a. There is a total of three resonance structures (including the original structure).
b. There is one additional resonance structure.
NH₂
c. There is a total of five resonance structures (including the original structure).
: OH
While carbon mostly forms 4 bonds (and has a full octet), this is not always true. During reactions, carbon intermediates often only make three bonds and do not follow this rule.
a. Which of these three carbon atoms (to the right) has an incomplete octet?
b. How many more electrons would be needed to fill each octet?
c. What are the formal charges on these carbon atoms?
Which of the named compounds have correct structures? *
2 poin
ҫн,
CH,CH,Br
Br
I. meta chlorotoluene
II. bromomethyltoluene
I. para bromophenol
NH,
OCH,
NO,
Cl
IV. ortho nitroanisole
V. 2,4.6-trichloroaniline
O A. I, II, IV
O B. I, II, IV
O c. I, IV, V
O D. II, II, V
Arrange the following in order of increasing ability to hydrogen bond
3 poim
(lowest first)
I.
CH3-H
II. CH;S-H
III. CH;O-H
V. НО-Н
A. I, II, II, IV
O B. II, I, V, I
O c. I, IV, I, II
D. I, IV, II, II
Chapter 1 Solutions
Organic Chemistry (9th Edition)
Ch. 1.2C - a. Nitrogen has relatively stable isotopes...Ch. 1.4 - Draw Lewis structures for the following compounds....Ch. 1.5 - Write Lewis structures for the following molecular...Ch. 1.5 - Circle any lone pairs (pairs of nonbonding...Ch. 1.6 - Use electronegativities to predict the direction...Ch. 1.8 - Prob. 1.6PCh. 1.9B - Draw the important resonance forms for the...Ch. 1.9B - Prob. 1.8PCh. 1.9B - Prob. 1.9PCh. 1.9B - Use resonance structures to identify the areas of...
Ch. 1.10A - Draw complete Lewis structures for the following...Ch. 1.10B - Give Lewis structures corresponding to the...Ch. 1.10B - Prob. 1.13PCh. 1.11 - Compute the empirical and molecular formulas for...Ch. 1.16 - a. Use your molecular models to make ethane, and...Ch. 1.17 - a. Predict the hybridization of the oxygen atom in...Ch. 1.17 - Predict the hybridization geometry and bond angles...Ch. 1.17 - Predict the hybridization, geometry, and bond...Ch. 1.17 - Prob. 1.19PCh. 1.17 - Allene, CH2=C=CH2, has the structure shown below...Ch. 1.17 - 1. Draw the important resonance forms for each...Ch. 1.18B - Prob. 1.22PCh. 1.18B - Two compounds with the formula CH3CH=NCH3 are...Ch. 1.19B - Prob. 1.24PCh. 1.19B - Give the relationship between the following pairs...Ch. 1 - a. Draw the resonance forms for SO2 (bonded OSO)....Ch. 1 - Name the element that corresponds to each...Ch. 1 - Prob. 1.28SPCh. 1 - For each compound, state whether its bonding is...Ch. 1 - a. Both PCl3 and PCl5 are stable compounds Draw...Ch. 1 - Draw a Lewis structure for each species a. N2H4 b....Ch. 1 - Prob. 1.32SPCh. 1 - Prob. 1.33SPCh. 1 - Draw Lewis structures for a. two compounds of...Ch. 1 - Prob. 1.35SPCh. 1 - Some of the following molecular formulas...Ch. 1 - Prob. 1.37SPCh. 1 - Give the molecular formula of each compound shown...Ch. 1 - 1. From what you remember of electronegativities,...Ch. 1 - For each of the following structures, 1. Draw a...Ch. 1 - Prob. 1.41SPCh. 1 - Prob. 1.42SPCh. 1 - Prob. 1.43SPCh. 1 - Prob. 1.44SPCh. 1 - For each pair of ions, determine which on is more...Ch. 1 - Use resonance structures to identify the areas of...Ch. 1 - Prob. 1.47SPCh. 1 - In 1934, Edward A. Doisy of Washington University...Ch. 1 - If the carbon atom in CH2Cl2 were fat. there would...Ch. 1 - Cyclopropane (C3H6, a three-membered ring) is more...Ch. 1 - Prob. 1.51SPCh. 1 - Prob. 1.52SPCh. 1 - In most amines, the nitrogen atom is sp3...Ch. 1 - Predict the hybridization and geometry of the...Ch. 1 - Draw orbital pictures of the pi bonding in the...Ch. 1 - Prob. 1.56SPCh. 1 - Prob. 1.57SPCh. 1 - Which of the following compounds show cis-trans...Ch. 1 - Give the relationships between the following pairs...Ch. 1 - Dimethyl sulfoxide (DMSO) has been used as an...
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- 2. Consider the resonance structures below may only A C. yongary] B C D a. On each structure (A-D) show all lone pair electrons. b. Provide arrows that show electron movement from A to B, B to C, and C to D. Which is the "most contributing” resonance form (A, B, C, or D)? Explain your choice. d. Draw the resonance hybrid for this molecule (use “delta” 8+ or - to show partial charges).arrow_forwardThe Structure of Hydrocarbons 1. Draw the four carbon bonding patterns commonly seen in hydrocarbons and all other organic compounds. Construct the Lewis structures of the following compounds by combining the carbon atoms with the appropriate bonding patterns and the required number of hydrogen atoms. 2. a. hexane: CH,CH,CH,CH,CH,CH, b. 3-hexene: CH,CH,CH=CHCH,CH, c. 2-hexyne: CH,C=CCH,CH,CH, 3. There are three distinct bond angles formed in the four bonding patterns of carbon. What are they and in which bonding pattern(s) is each seen?arrow_forwardDraw the Lewis structure of the missing reactant. Make sure to include lone pairs and non-zero formal charges. HCl + CI + CH;CH,OH Click and drag to start drawing a structure. toarrow_forward
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- 1. What is the relationship between the following compounds? H :0: H H:0: H H-C=C-C-C-C-H H-C-C-C=Ċ-H H HH H. H-C-H B. constitutional isomers C. the same structure A. isotopes D. composed of different elements E. no relationship 2. What is the correct Lewis structure for HN3, including the formal charges? CIHarrow_forwardSC ! F1 Q @ 2 F2 W #3 Which structure has a formal charge of -1 on the carbon shown with a "C"? Note that the atom of interest in each case includes any hydrogens or lone pairs that are present. =C- (b) (c) (d) O a.. O b.. O c.. O d.. A Moving to another question will save this response. >> 20 F9 F10 F3 F4 E @ $ 4 R % F5 T MacBook Air F6 6 Y & 7 F7 U * 00 8 DII FB ( 9 ) 0 I P a F11arrow_forwardDraw Lewis structures for tye following molecules. a.) Atom "X" has 4 valence electrons and Atom "Y" has 6 valence electrons. Draw the Lewis structure for the molecule XY2, showing all lone pairs and formal charges when necessary b.) Atom "M" has 5 valence electrons and Atom "L" has 7 valence electrons. Draw the Lewis structure for the molecule M2L4, showing all lone pairs and formal charges when necessaryarrow_forward
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