Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Question
Chapter 5, Problem 5.26P
Interpretation Introduction
Interpretation:
Bond angles of
Concept Introduction:
VSEPR Theory:
The basis for this theory is the electron pair that is bonded electron present in either single or double bonds or lone pair electrons, present in the valence shell tends to repel each other which then tend to be in position in order to minimize the repulsions.
According to VSEPR theory, the geometry is predicted by the minimizing the repulsions between electron-pairs in the bonds and lone-pairs of electrons. The VSEPR theory is summarized in the given table as,
- • Bond angle is the angle between two bonds of a molecule and it is determined based on the electron-domain geometry.
- • Electro-domain geometry includes both bond pairs and lone pairs of central atom for determining the geometry of molecule.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Explain the hybridisation of electron orbitals in a carbon atom (sp, sp2 and sp3), giving a detailed explanation,
supported by suitable examples, of how sigma (s) and pi (p) bonds are formed. 2 Explain why alkenes are much more
reactive than alkanes towards chlorine (C12) or bromine (Br2) in the dark at room temperature, and why alkanes do not
react with HCI (g) or HBr (g) whereas alkenes do. please provide a diagram as well
Estimate the strain energy of the following 2,3-dimethylbutane conformation.
Use strain energy increments from the table given in the question, and be sure to specify your units, e.g.kJ/mol. Calculate energy to the nearest 0.1 energy unit.
Strain Energy Increments
strain
CH3
Ø
CH3
H.
H
CH3
The strain energy is
Interaction
HH eclipsing
H→ CH3 eclipsing
CH3 CH3 eclipsing
CH3 CH3 gauche
→
→
kJ/mol kcal/mol
4.0
6.0
11.0
3.8
1.0
1.4
2.6
0.9
(a) Describe the molecular geometry expected for 1,2,3-butatriene (H2C=C=C=CH2). (b) Two stereoisomers are expected for 2,3,4-hexatriene (CH3CH=C=C=CHCH3). What should be the relationship between these two stereoisomers?
Chapter 5 Solutions
Organic Chemistry
Ch. 5.1 - Calculate the index of hydrogen deficiency for...Ch. 5.1 - Prob. 5.2PCh. 5.2 - Write the IUPAC name of each alkene. (a) (b)Ch. 5.2 - Prob. 5.4PCh. 5.2 - Prob. 5.5PCh. 5.2 - Prob. 5.6PCh. 5.2 - Prob. 5.7PCh. 5.2 - Prob. 5.8PCh. 5 - Predict all approximate bond angles about each...Ch. 5 - Prob. 5.10P
Ch. 5 - The structure of 1,2-propadiene (allene) is shown...Ch. 5 - Prob. 5.12PCh. 5 - Draw structural formulas for these alkenes. (a)...Ch. 5 - Name these alkenes and cycloalkenes.Ch. 5 - Prob. 5.15PCh. 5 - Prob. 5.16PCh. 5 - Prob. 5.17PCh. 5 - For each molecule that shows cis, trans isomerism,...Ch. 5 - -Ocimene, a triene found in the fragrance of...Ch. 5 - Prob. 5.20PCh. 5 - Prob. 5.21PCh. 5 - Prob. 5.22PCh. 5 - Prob. 5.23PCh. 5 - Prob. 5.24PCh. 5 - Measure the CH3,CH3 distance in the...Ch. 5 - Prob. 5.26PCh. 5 - Measure the CCC and CCH bond angles in the...Ch. 5 - Prob. 5.28PCh. 5 - Prob. 5.29PCh. 5 - Prob. 5.30PCh. 5 - Prob. 5.31PCh. 5 - Prob. 5.32PCh. 5 - Prob. 5.33PCh. 5 - Pyrethrin II and pyrethrosin are two natural...Ch. 5 - Prob. 5.35PCh. 5 - Prob. 5.36PCh. 5 - Bromine adds to cis- and trans-2-butene to give...
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
- Construct models of all the possible stereoisomers of 1,2-dichlorocyclopropane. Using your models, draw structures for and name the isomers. Label each chirality centre R or S. Indicate which pairs are related as enantiomers and which as diastereoisomers.arrow_forwardWhich one of the following represents the HOMO of 1,3,5-hexatriene? IV || f V 8 |||arrow_forwardProvide a complete, labeled orbital diagram for 1-fluoro-butadiene (FHC=CH-CH=CH2). Indicate all bond types (including which orbitals have overlapped to form each bond) and bond angles.arrow_forward
- 1. An experimental technique called ¹3C-Nuclear Magnetic Resonance Spectroscopy allows chemists to tell how many different kinds of carbon there are in a molecule and whether carbons are primary (1°), secondary (2°), tertiary (3°), or quaternary (4°). Give dash (Kekule) structures (i.e., use lines for electron pair bonds) for the following compounds having a molecular formula C6H12. Also, on each structure, identify carbons as 1º, 2º, 3º, 4º; tell how many different kinds of C's there are; and designate which C's are equivalent. a) A compound having only single bonds and only secondary carbons. b) A compound having only single bonds and primary, secondary, and tertiary carbons. c) A compound having only single bonds and only primary, secondary, and quaternary carbons. d) A compound having only single bonds and primary, secondary, tertiary, and quaternary carbons.arrow_forwardThe barrier to C-C bond rotation in bromoethane is 15 kJ/mol. What energy can you assign to an H-Br eclipsing interaction? Use strain energy increments from the table below in your calculation. Interaction (Specify units, kJ/mol; Calculate to nearest 0.1 energy units) H → H eclipsed H → CH3 eclipsed CH3 → CH3 eclipsed CH3 CH3 gauche Cause Torsional strain Mostly torsional strain Torsional and steric strain Steric strain (kJ/mol) Energy cost 4.0 6.0 11.0 3.8 (kcal/mol) 1.0 1.4 2.6 0.9arrow_forwardThe pentadienyl radical, H2C“CH¬CH“CH¬CH2#, has its unpaired electron delocalized over three carbon atoms.(a) Use resonance forms to show which three carbon atoms bear the unpaired electron.(b) How many MOs are there in the molecular orbital picture of the pentadienyl radical?(c) How many nodes are there in the lowest-energy MO of the pentadienyl system? How many in the highest-energy MO?(d) Draw the MOs of the pentadienyl system in order of increasing energy. (continued)762 CHAPTER 15 Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy(e) Show how many electrons are in each MO for the pentadienyl radical (ground state).(f) Show how your molecular orbital picture agrees with the resonance picture showing delocalization of the unpairedelectron onto three carbon atoms.(g) Remove the highest-energy electron from the pentadienyl radical to give the pentadienyl cation. Which carbon atomsshare the positive charge? Does this picture agree with the resonance picture?(h) Add an…arrow_forward
- 2. Calculate AH for the reaction; C₂H₂ (s) → 2 C (s) + H₂ (g), from the following Data; 1) CO2 (g) → C (s) +O2 (g) 2) 2 H₂O (1)→ → 2 2 H2 H2 (g) + O2 (g) 3) 2 C2H2 (s) + 5 O2 (g) → 4 CO2 (g) + 2 H₂O (1) ΔΗ = +394 kJ ΔΗ = +572 kJ AH = -2600 kJarrow_forwardWrite structures for the cis and trans isomers of (a) 1,2-dichlorocyclopentane and (b) 1,3- dibromocyclobutane. (c) Are cis-trans isomers possible for 1,1-dibromocyclobutane?arrow_forwardThe energy difference between a tert-butyl group going from equatorial to axial in a cyclohexane is 18.3 kJ/mol. When two of the carbon atoms are replaced with oxygen atoms (molecule B) the energy difference between the two chair conformations drops to 5.9 kJ/mol. Explain this difference. (Hint: Consider what makes putting groups axial unfavorable).arrow_forward
- Is isomerization of cis and trans 5-methyl-2,4-octadiene possible at room temperature? Explainarrow_forward2,3-Dibromoprop-1-ene (C3H4Br2) has four H atoms. Suppose that any of these H atoms can be replaced by a Cl atom to yield a molecule with the formula C3H3Br,Cl. (a) Identify two H atoms where this substitution would yield constitutional isomers of C3H3Br,CI; (b) enantiomers of C3H3Br,Cl; (c) diastereomers of C3H3Br,Cl. H нн H Br Br 2,3-Dibromoprop-1-enearrow_forwardI. Molecule's Degree of Unsaturation* *to avoid confusion, we shall use "degree of unsaturation" to refer to the number of pi bonds or number of rings present in the molecule as a result of the loss of hydrogen atoms when referenced using the alkane formula of C,„H2n+2" The numerical value for the degree of unsaturation = 1 means that a molecule of hydrogen, H,, or two atoms of hydrogen are lost and instead 1 pi bond OR 1 ring is seen in the molecule. For this exercise, determine the degree of unsaturation of each of the following compounds: CH3 1. 2,3,3-Trimethyl-1,4,6-octatriene CH3 6. CH3 2. 3-Ethyl-2,2,-dimethyl-3-heptene `CH3 3. 2-Methyl-1,5-hexadiene 8. 7. ÇH3 H. CH3 4. 4-tert-Butyl-2-methylheptane Answers: 1. L2. 3. _4. 5. 6. _7. 8. 5.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Types of bonds; Author: Edspira;https://www.youtube.com/watch?v=Jj0V01Arebk;License: Standard YouTube License, CC-BY