Why does acetone [(CH3)2C=O, dipole moment = 2.69 D] have a larger dipole moment than phosgene [Cl₂C=O, dipole moment = 1.17 D]? Note: electronegativities C = 2.5, Cl = 3.2, O = 3.5, H = 2.2 Select one: O A. In phosgene, the resultant of the C-Cl bond dipole moments is opposite to and partially cancels the C=O dipole moment. In acetone, the resultant of the C-H bond dipole moments (although small) adds to the C=O dipole moment. O B. Phosgene has a tetrahedral geometry while acetone possesses a trigonal geometry. OC. The C-H bond dipole moments of acetone are greater in magnitude than C-Cl bond dipole moments of phosgene. O D. In phosgene the C-Cl bond dipoles cancel out each other.

Why does acetone [(CH3)2C=O, dipole moment = 2.69 D] have a larger dipole moment than phosgene [Cl₂C=O, dipole moment = 1.17 D]? Note: electronegativities C = 2.5, Cl = 3.2, O = 3.5, H = 2.2 Select one: O A. In phosgene, the resultant of the C-Cl bond dipole moments is opposite to and partially cancels the C=O dipole moment. In acetone, the resultant of the C-H bond dipole moments (although small) adds to the C=O dipole moment. O B. Phosgene has a tetrahedral geometry while acetone possesses a trigonal geometry. OC. The C-H bond dipole moments of acetone are greater in magnitude than C-Cl bond dipole moments of phosgene. O D. In phosgene the C-Cl bond dipoles cancel out each other.

Introduction to General, Organic and Biochemistry

11th Edition

ISBN:9781285869759

Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Chapter10: Organic Chemistry

Section: Chapter Questions

Problem 10.22P: 10-22 Suppose you forget to take into account the presence of the unshared pair of electrons on...

See similar textbooks

Similar questions

The bonding between the carbon and oxygen in a ketone can be described as C(sp2)-0(sp²), o-bond and C(p)-O(p), л-bond. How would you describe the bonding between carbon and oxygen in a ketene? Sketch the orbitals used to make the bonds in the ketene. H a ketene
Phosgene, Cl2C = O, has a lower dipole moment than formaldehyde H2C = O. Explain why.
7 The 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.
Sodium triacetoxyborohydride, NaBH(OAc)3, is a mild reducing agent that reduces aldehydesmuch more quickly than ketones. It can be used to reduce aldehydes in the presence of ketones,such as in the following reaction:CH3 C CH2O OC H CH3 C CH2OCH2OHNaBH(OAc)3CH3COOH(a) Draw a complete Lewis structure for sodium triacetoxyborohydride.(b) Propose a mechanism for the reduction of an aldehyde by sodium triacetoxyborohydride
Methyl isocyanate, CH3 -N= C = O, is used in the industrial synthesis of a type of pesticide and herbicide known as a carbamate. As a historical note, an industrial accident in Bhopal, India, in 1984 resulted in leakage of an unknown quantity of this chemical into the air. An estimated 200,000 people were exposed to its vapors, and over 2000 of these people died. Q.) Write a Lewis structure for methyl isocyanate and predict its bond angles. What is the hybridization of its carbonyl carbon? Of its nitrogen atom?
Rank the following compounds in order of decreasing dipole moment. H H H H O|||||| O|||||II || 1>||| O I>II>III H ||| ||||
(G) Show the delocalization Of Charges in the following Structures. Draw the resonance forms and indicate the movement of electrons with curved arrows (ii) CH2= CH- o+
List the bond lenghts between the carbon and the oxygen atoms for the carboxylic acid and carboxylate ion and rank from shortest to longest. carboxylic acid carboxylate ion c-o c=o provide an explanation for the differences in the bond lengths and the orientation of the dipole moment between the acid and ion.
compound HO at 6 and NO2 at 1
10-22 Suppose you forget to take into account the presence of the unshared pair of electrons on nitrogen in the molecule NH3. What would you then predict for the H—N—H bond angles and the geometry (bond angles and shape) of ammonia?
2. Account for the bond angle differences between (i) H-C-H (109.5°) in methane and H-S-H (90°); H-C-H (109.5°) and H-O-H (107.5°) in water The H-S-H has two lone pairs; The H-O-H has two lone pairs The H-S-H has no hybridization at p-orbitals; The H-O-H has two lone pairs The H-S-H has two lone pairs; The H-O-H has no hybridization at p-orbitals The H-S-H has no hybridization at p-orbitals; The H-O-H has no hybridization at p- orbitals
Acetonitrile (CH3CN) has resonance at 1.97 ppm, whereas methyl chloride (CH3Cl) has resonance at 3.05 ppm, even though the dipole moment of acetonitrile is 3.92 D and that of methyl chloride is only 1.85 D. The larger dipole moment for the cyano group suggests that the electronegativity of this group is greater than that of the chlorine atom. Explain why the methyl hydrogens on acetonitrile are actually more shielded than those in methyl chloride, in contrast with the results expected on the basis of electronegativity