Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 1.16, Problem 1.15P
- a. Use your molecular models to make ethane, and compare the model with the preceding structures.
- b. Make a model of propane (C3H3), and draw this model using dashed lines and wedges to represent bonds going back and coming forward.
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3. The following shows all resonance structures for the following molecule.
a. Draw in all implied lone pairs.
b. Draw in curved arrows that show the flow of electrons, making sure the arrows show the precise
starting point and destination of the electrons.
Label each arrow as: lp →→→л (p=lone pair)
c.
d.
Rank the resonance structures from most stable to least based on the number of formal charges and
atoms that lack an octet of electrons.
ol-of-o.
B
A
D
d-d-d-o
E
C
F
G
10. Build a model of CHBRCIF. Next, build a
model of the mirror image of your first
molecule. How are these molecules related?
B. Cycloalkanes
1) Construct a model of the cyclic alkane: cyclopentane (C5H₁0). Because the five carbon atoms are locked in a ring,
rotation about the single bonds is restricted; the plane of the ring a fixed geometry within the molecule. Toggle between
full Lewis structures and skeletal structures by clicking the C-H tool.
Model 1: Use the solid wedge tool to attach a methyl group to each of two different carbon atoms in the cyclopentane.
Note the five carbons of the ring are in the plane of the paper, and the solid wedge indicates both methyls project forward,
in front of the plane of the paper.
Model 2: Use the solid wedge tool to attach first methyl group to one of two different carbon atoms in the cyclopentane,
and use the dashed wedge tool to attach the second. Note the solid wedge indicates that one methyl projects forward, in
front of the plane of the paper. The dashed wedge indicates the other methyl extends back, behind the plane of the paper.
Click the broom to tidy up the…
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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- 3. Draw the Lewis-dot structure for C4H10 below. Remember the Lewis-dot structure is the same as the Expanded structure. A. What is the main intermolecular force acting on this molecule? B. Is this molecule polar or nonpolar? Provide a brief explanation (2-3 sentences) for your answer.arrow_forward1) For each condensed or skeletal structure below: A. Draw a complete Lewis structure. Note: show all non-bonding electron pairs. B. Indicate the hybridization of all C, O, and N atoms in each of the molecules. C. Label each of the indicated bonds (marked by an arrow) as either a sigma or pi bond. (Note: Remember, e.g. that a double bond is made up of both a o and a π bond). Also indicate which orbitals overlap to form the bond (e.g., Ols-2sp3). D. For atoms having lone pairs in the molecules below, indicate in which orbitals the lone pairs are located. E. Which of the bonds indicated by arrows is shorter? a) c) H CH3 C=CHC=C-CH g) (CH3)3CCN CH3 CH₂CH=CHCECH b) d) CH3 Lo LOH f) CH₂CH(CH3)SH h) (CH3)2CH(CH₂)3Brarrow_forward2. 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 byarrow_forward
- 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). : OHarrow_forward1. For each molecule and ion below, indicate the total number of valence electrons. Based on that number of electrons, draw a valid Lewis structure.2. Use VSEPR theory to determine the electron arrangement and the geometry of the molecule around the central atom(s). A table of geometries is attached.3. Build the molecule using the molecular models provided in the lab. Sketch your model well enough to show the geometry. Include bond angles.4. Using your understanding of electronegativity and its trends in the Periodic Table, determine if polar bonds exist in the molecule.5. Using bond polarity and molecular shape, determine if the molecule has an overall dipole. If all the bonds are nonpolar, the molecule is nonpolar. If polar bonds are present, then consider the shape to determine if the molecule has an overall dipole.arrow_forward3. Write the Lewis dot (electron dot) symbol for each covalent molecule. Remember the number of unpaired electrons in the Lewis dot symbol of the atom determines the number of bonds each atom makes. If your molecule has unpaired electrons you are not done. If your molecule has the wrong number of bonds for some atoms it is wrong. Try a different arrangement of atoms. Working left to right will help you. Show loan pairs. a. CH3CH₂OH b. CHCl, Br C. CH3NH₂ d. CHỊCH,CH,CH,CH3 e. CH3SCH 3 4. Write the Lewis dot (electron dot) symbol for each covalent molecule. Remember the number of unpaired electrons in the Lewis dot symbol of the atom determines the number of bonds each atom makes. If your molecule has unpaired electrons you are not done. If your molecule has the wrong number of bonds for some atoms it is wrong. Try a different arrangement of atoms. Working left to right will help you. Show loan pairs. a. HCN b. CH3COOH c. H₂CCONHCH3 d. HCCH e. C6H12arrow_forward
- The 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_forward2. 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_forwardAnswer the following questions about compound A. a. Label the shortest C-C single bond. b. Label the longest C-C single bond. c. Considering all the bonds, label the shortest C-C bond. d. Label the weakest C-C bond. e. Label the strongest C-H bond. f. Explain why bond (1) and bond (2) are different in length, even though they are both C-C single bonds. (2)arrow_forward
- Change ethane into 1,2-ethanediol (HOCH2CH2OH) by removing one hydrogen atom from each carbon atom and replacing with a hydroxide (-OH) group. Build a model of the 1,2-ethanediol molecule. A. Identify the electron-pair and molecular geometry around each carbon and oxygen atom. B. What are the bond angles for H-C-H? For H-C-C? For C-C-O? For C-O-H? C. Draw two different structures of the molecule in which the –OH groups on the two carbon atoms have different orientations with respect to each other.arrow_forwardDetermine if the structural formula below is an acceptable Lewis structures for organic compounds. Point out the problems in cases where structure is invalid. •. :OH CH- .CH3 A. Non of the options here are correct. B. This is not a correct Lewis structural formula because carbon cannot have five bonds. C. This structure is a correct Lewis structural formula. D. This is not a correct Lewis structure because the methyl group does not have an octet of electrons.arrow_forwardDetermine if the structural formula below are acceptable Lewis structures for organic compounds. Point out the problems in cases where structure is invalid. CH3 CH;-N-CH-CH3 ČH3 A. This structure is correct because the valance of Nitrogen is complete. B. This is not a correct Lewis structure because Nitrogen can accommodate more atoms. C. This is not a correct Lewis structure because Nitrogen has a charge if it does not have three bonds. D. This is a correct Lewis structure.arrow_forward
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