Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 1.17, Problem 1.21P
- 1. Draw the important resonance forms for each compound.
- 2. Label the hybridization and bond angles around each atom other than hydrogen.
- 3. Use a three-dimensional drawing to show where the electrons are pictured to be in each resonance form.
- a. HCONH2
- b. b [CH2OH]+
- c. [CH2CHO] −
- d. [CH3CHNO2] −
- e. [CH2CN]−
- f. B(OH)3
- g. ozone (O3, bonded OOO)
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Label the polar bonds in each molecule. Indicate the direction of the net dipole (if there is one).
Br
CI
a. CHBR3
b. CH3CH2OCH2CH3
C.
d.
Br
CI
Ф
-OH
Identify the structure below that represent the same compound shown above
O A.
B.
OC.
OH
OH
.OH
CI
.CI
CI
Change 1,2-ethanediol into 1,2 ethenediol (HOCHCHOH) by removing one hydrogen atom from each carbon atom and replacing with a double bond between the carbon atoms. Be sure to add the second rod to represent the double bond.
Draw a Lewis structure for 1,2-ethenediol.
A. Identify the electron-pair and molecular geometry around each carbon and oxygen atom.
B. What are the bond angles for H-C-C? For C-C-O? For C-O-H?
C. Draw two different structures of the molecule in which the –OH group on the two carbon atoms occupy different orientations with respect to each other.
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...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Change 1,2-ethenediol into 1,2 ethynediol (HOCCOH) by removing one hydrogen atom from each carbon atom and replacing with a triple bond between the carbon atoms. Be sure to add the third rod to represent the triple bond. Draw a Lewis structure for 1,2-ethynediol. A. Identify the electron-pair and molecular geometry around each carbon and oxygen atom. B. What are the bond angles for C-C-O? For C-O-H? C. Can the molecule interconvert or “flip” between different structures in which the –OH group on the two carbon atoms occupy different orientations with respect to each other? If so, how does this happen? If not, why?arrow_forwardChange 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_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
- 3. Draw all possible resonance structures to show the delocalization in the following molecule. Use curved arrow(s) to show the movement of electron pairs. Determine and circle which resonance is the most stable. Show the lone pair of electrons if necessary. a. b. C. d. CH3 å (+) CH3 : NH₂arrow_forwardREPRESENTATIONS OF ORGANIC MOLECULES Identifying isomers and resonance structures Determine the relationship between Structure A and Structure B in each row of the table. Structure A Structure B Relationship H. o isomers H. H H -H H-C- C-O -H- O resonance structures H H. H H Н—С—Н o neither H o isomers H :0: :0-H H. H H- C-C C-H H-C=C C=C-H O resonance structures H. H. H o neither o isomers :o: H H. H- O resonance structures H H H. H o neither 72°F DELL :ö: IIarrow_forwardWhich of the following molecules has only single bonds. A. CHCHCH3 B. CH2CHCH3 C. CH3CH2CCH D. CH3CH3 E. CH2CH2 Which of the following molecules has a carbon-to-carbon double bond? A. CH3CCH B. CHCH C. CH3CH3 D. CH3CH2CH3 E. CH2CHCH3arrow_forward
- H₂C a. How many polar bond(s) is (are) present in this molecule? b. What is the most electronegative atom present in this molecule? c. What is the least electronegative atom present in this molecule? N * For the C-0 bond, what is the direction of the dipole moment (from 3+ to 2-)? Use either 'up' or 'down' for your answer inaný 0=6 $ -0 to de % CH3 A hparrow_forwardDraw a valid Lewis structure for each compound. a. Ng b. (CH,OH)* (CH;CH2) d. HNNH е. НаBN C.arrow_forwardConsider a molecule of methanimine (CH3N) compared to a molecule of methylamine (CH5N). The C-N bond in methanimine is than the C-N bond in methylamine. A. longer and stronger B. longer and weaker C. shorter and stronger D. shorter and weaker E. the same strength and length asarrow_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_forwardHow are the molecules or ions in each pair related? Classify them as resonance structures, isomers, or neither. CH3 a. CH,-Ö-CH,CH, and C. and b. and CH3-C=C-CH3 d. CH;CH,CH3 CH,CH,ČH2 and ннarrow_forwardFill in all H's and lone pairs in each compound. b. c--c а. С—С—с—С С. С —С—С d. C-Ĉ-N-C е.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
Nomenclature: Crash Course Chemistry #44; Author: CrashCourse;https://www.youtube.com/watch?v=U7wavimfNFE;License: Standard YouTube License, CC-BY