![Organic Chemistry](https://www.bartleby.com/isbn_cover_images/9781305080485/9781305080485_largeCoverImage.gif)
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 1.SE, Problem 50AP
Most stable organic species have tetravalent carbon atoms, but species with trivalent carbon atoms also exist. Carbocations are one such class of compounds.
![Chapter 1.SE, Problem 50AP, Most stable organic species have tetravalent carbon atoms, but species with trivalent carbon atoms](https://content.bartleby.com/tbms-images/9781305080485/Chapter-1/images/80485-1.se-50ap-question-digital.jpg)
(a) How many valence electrons does the positively charged carbon atom have?
(b) What hybridization do you expect this carbon atom to have?
(c) What geometry is the carbocation likely to have?
Expert Solution & Answer
![Check Mark](/static/check-mark.png)
Trending nowThis is a popular solution!
![Blurred answer](/static/blurred-answer.jpg)
Students have asked these similar questions
Octocrylene is an ingredient found in topical sunscreens. It is a water-resistant molecule
that helps protect skin against harmful UVA and UVB radiation.
Octocrylene
Please answer the following questions:
(a) What is the hybridisation of each nonhydrogen atom?
(b) Are there two unique configurations possible about the C=C double bond? Please
explain your answer.
(c) Which of the two C-C bonds indicated by the arrows would you expect to be shorte.?
Please explain your answer.
The drawing below shows the overlap of two hybrid orbitalsto form a bond in a hydrocarbon. (a) Which of the followingtypes of bonds is being formed: (i) C¬C σ, (ii) C¬C π,or (iii) C¬H σ? (b) Which of the following could be theidentity of the hydrocarbon: (i) CH4, (ii) C2H6, (iii) C2H4, or(iv) C2H2?
The structure of caffeine is shown below.
(a) Complete the Lewis structure.
(b) How many pi bonds are present in caffeine? How many sigma bonds?
(c) Identify the hybridization of the carbon atoms.
(d) What is the value of the O-C-N angle?
Chapter 1 Solutions
Organic Chemistry
Ch. 1.3 - Give the ground-state electron configuration for...Ch. 1.3 - How many electrons does each of the following...Ch. 1.4 - Prob. 3PCh. 1.4 - Convert the following representation of ethane,...Ch. 1.4 - What are likely formulas for the following...Ch. 1.4 - Prob. 6PCh. 1.4 - Prob. 7PCh. 1.7 - Draw a line-bond structure for propane, CH3CH2CH3....Ch. 1.7 - Convert the following molecular model of hexane, a...Ch. 1.8 - Draw a line-bond structure for propene, CH3CH=CH2....
Ch. 1.8 - Draw a line-bond structure for 1, 3-butadiene,...Ch. 1.8 - Following is a molecular model of aspirin...Ch. 1.9 - Draw a line-bond structure for propyne, CH3C≡CH....Ch. 1.10 - Prob. 14PCh. 1.12 - Prob. 15PCh. 1.12 - Prob. 16PCh. 1.12 - The following molecular model is a representation...Ch. 1.SE - Convert each of the following molecular models...Ch. 1.SE - The following model is a representation of citric...Ch. 1.SE - The following model is a representation of...Ch. 1.SE - The following model is a representation of...Ch. 1.SE - How many valence electrons does each of the...Ch. 1.SE - Give the ground-state electron configuration for...Ch. 1.SE - Prob. 24APCh. 1.SE - Prob. 25APCh. 1.SE - Draw an electron-dot structure for acetonitrile,...Ch. 1.SE - Draw a line-bond structure for vinyl chloride,...Ch. 1.SE - Fill in any nonbonding valence electrons that are...Ch. 1.SE - Convert the following line-bond structures into...Ch. 1.SE - Convert the following molecular formulas into...Ch. 1.SE - Prob. 31APCh. 1.SE - Oxaloacetic acid, an important intermediate in...Ch. 1.SE - Prob. 33APCh. 1.SE - Potassium methoxide, KOCH3, contains both covalent...Ch. 1.SE - What is the hybridization of each carbon atom in...Ch. 1.SE - Prob. 36APCh. 1.SE - Prob. 37APCh. 1.SE - What bond angles do you expect for each of the...Ch. 1.SE - Propose structures for molecules that meet the...Ch. 1.SE - What kind of hybridization do you expect for each...Ch. 1.SE - Pyridoxal phosphate, a close relative of vitamin...Ch. 1.SE - Prob. 42APCh. 1.SE - Prob. 43APCh. 1.SE - Quetiapine, marketed as Seroquel, is a heavily...Ch. 1.SE - Tell the number of hydrogens bonded to each carbon...Ch. 1.SE - Why do you suppose no one has ever been able to...Ch. 1.SE - Allene, H2C=C=CH2, is somewhat unusual in that it...Ch. 1.SE - Allene (see Problem 1-47) is structurally related...Ch. 1.SE - Complete the electron-dot structure of caffeine,...Ch. 1.SE - Most stable organic species have tetravalent...Ch. 1.SE - A carbanion is a species that contains a...Ch. 1.SE - Divalent carbon species called carbenes are...Ch. 1.SE - There are two different substances with the...Ch. 1.SE - There are two different substances with the...Ch. 1.SE - There are two different substances with the...Ch. 1.SE - Prob. 56APCh. 1.SE - Among the most common over-the-counter drugs you...
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
- All carbon-to-carbon bond lengths are identical in benzene. Does this argue for or against the presence of C=C bonds in benzene? Explain.arrow_forwardDichloroethylene (C2H2Cl2) has three forms (isomers), eachof which is a different substance. (a) Draw Lewis structures ofthe three isomers, all of which have a carbon–carbon doublebond. (b) Which of these isomers has a zero dipole moment?(c) How many isomeric forms can chloroethylene, C2H3Cl,have? Would they be expected to have dipole moments?arrow_forwardButadiene, C4H6, is a planar molecule that has the followingcarbon–carbon bond lengths: (a) Predict the bond angles around each of the carbon atoms and sketch the molecule. (b) From left to right, what is the hybridization of each carbon atom in butadiene? (c) The middle C—C bond length in butadiene (1.48 Å) is a little shorter than the average C—C single bond length (1.54 Å). Does this imply that the middle C—C bond in butadiene is weaker or stronger than the average C—C single bond? (d) Based on your answer for part (c), discuss what additional aspects of bonding in butadiene might support the shorter middle C—C bond.arrow_forward
- In following decomposition reaction:2C3H8(g)⟶ C2H4(g)+ C3H6(g) + CH4(g) + H2(g)For each of the four carbon compounds, do the following: (a) Draw Lewis structure.(b) Predict the geometry about the carbon atom.(c) Determine the hybridization of each type of carbon atom.arrow_forwardGive the (a) bond order and (b) hybridization state of each carbon atom of propadiene, H2CCCH2.arrow_forwardButadiene, C4H6, is a planar molecule that has the followingcarbon–carbon bond lengths:(a) Predict the bond angles around each of the carbon atomsand sketch the molecule. (b) From left to right, whatis the hybridization of each carbon atom in butadiene?(c) The middle C¬C bond length in butadiene (1.48 Å) isa little shorter than the average C¬C single bond length(1.54 Å). Does this imply that the middle C¬C bond in butadieneis weaker or stronger than the average C¬C singlebond? (d) Based on your answer for part (c), discuss what additional aspects of bonding in butadiene might supportthe shorter middle C¬C bond.arrow_forward
- Propylene, C3H6, is a gas that is used to form the importantpolymer called polypropylene. Its Lewis structure is given. (a) What is the total number of valence electrons in the propylenemolecule? (b) How many valence electrons are usedto make σ bonds in the molecule? (c) How many valenceelectrons are used to make π bonds in the molecule? (d) Howmany valence electrons remain in nonbonding pairs in themolecule? (e) What is the hybridization at each carbon atomin the molecule?arrow_forward(e) What is the molecular structure of BrF5? (f) Give a VSEPR structure of BrFs. Label relevant angles. (g) Is BrFs polar or non-polar? (h) What is the hybridization of the central atom, Br?arrow_forwardWhen one electron is added to an oxygen molecule, a superoxide ion (Oz) is formed. The addition of two elec- trons gives a peroxide ion (Oź ). Removal of an electron from O, leads to Ož. (a) Construct the correlation diagram for Oz. (b) Give the valence electron configuration for each of the following species: Ož, O2, 0z, 03 . (c) Give the bond order of each species. (d) Predict which species are paramagnetic. (e) Predict the order of increasing bond dissociation energy among the species.arrow_forward
- Azo dyes are organic dyes that are used for many applications,such as the coloring of fabrics. Many azo dyes arederivatives of the organic substance azobenzene, C12H10N2.A closely related substance is hydrazobenzene, C12H12N2.The Lewis structures of these two substances are(Recall the shorthand notation used for benzene.)(a) What is the hybridization at the N atom in each of thesubstances? (b) How many unhybridized atomic orbitalsare there on the N and the C atoms in each of the substances?(c) Predict the N¬N¬C angles in each of thesubstances. (d) Azobenzene is said to have greater delocalizationof its p electrons than hydrazobenzene. Discussthis statement in light of your answers to (a) and (b). (e) Allthe atoms of azobenzene lie in one plane, whereas thoseof hydrazobenzene do not. Is this observation consistentwith the statement in part (d)? (f) Azobenzene is an intensered-orange color, whereas hydrazobenzene is nearly colorless.Which molecule would be a better one to use in asolar…arrow_forwardIf an electron is removed from a fluorine molecule, an F+2molecular ion forms.(a) Give the molecular electron configurations for F2 and F+2 (for the MOs constructed from valence AOs).(b) Give the bond order of each species.(c) Predict which species should be paramagnetic.(d) Predict which species has the greater bond dissociation energy.arrow_forwardAzo dyes are organic dyes that are used for many applications,such as the coloring of fabrics. Many azo dyes arederivatives of the organic substance azobenzene, C12H10N2.A closely related substance is hydrazobenzene, C12H12N2.The Lewis structures of these two substances are given (Recall the shorthand notation used for benzene.)(a) What is the hybridization at the N atom in each of thesubstances? (b) How many unhybridized atomic orbitalsare there on the N and the C atoms in each of the substances?(c) Predict the N—N—C angles in each of thesubstances. (d) Azobenzene is said to have greater delocalizationof its π electrons than hydrazobenzene. Discussthis statement in light of your answers to (a) and (b). (e) Allthe atoms of azobenzene lie in one plane, whereas thoseof hydrazobenzene do not. Is this observation consistentwith the statement in part (d)? (f) Azobenzene is an intensered-orange color, whereas hydrazobenzene is nearly colorless.Which molecule would be a better one to use in…arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Chemistry: The Molecular ScienceChemistryISBN:9781285199047Author:John W. Moore, Conrad L. StanitskiPublisher:Cengage Learning
![Text book image](https://www.bartleby.com/isbn_cover_images/9781285199047/9781285199047_smallCoverImage.gif)
Chemistry: The Molecular Science
Chemistry
ISBN:9781285199047
Author:John W. Moore, Conrad L. Stanitski
Publisher:Cengage Learning
INTRODUCTION TO MOLECULAR QUANTUM MECHANICS -Valence bond theory - 1; Author: AGK Chemistry;https://www.youtube.com/watch?v=U8kPBPqDIwM;License: Standard YouTube License, CC-BY