HW4 Resonance structures for the "allyl carbanion" are shown below (I and II).CH CH=CH,CHFCH-CH2IIIWhich of the following statements regarding I and Il are correct?Select one:O A. The energy of the actual allyl carbanion is higher than the energyexpected for resonance structures I and II.B. Resonance structures I and II are nonequivalent resonance structures.C. The actual structure of an allyl carbanion is an average of structuresI and II, with both resonance structures weighted equally.D. In the actual allyl carbanion, both C,C bonds are unequal in length.

Actually structure is formed by the contribution of all resonating structures. Most stable…

Answered: Resonance structures for the "allyl…

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter5: Resonance

Section: Chapter Questions

Problem 19CTQ: The C=O double bond is called a “carbonyl bond.” Acetone and othercarbonyl compounds are introduced...

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The curved arrow notation introduced in Section 1.6B is a powerful method used by organic chemists to show the movement of electrons not only in resonance structures, but also in chemical reactions.Because each curved arrow shows the movement of two electrons, following the curved arrows illustrates what bonds are broken and formed in a reaction. Consider the following three-step process. (a) Add curved arrows in Step [1] to show the movement of electrons. (b) Use the curved arrows drawn in Step [2] to identify the structure of X. X is converted in Step [3] to phenol and HCl.
- What orbital(s) are the lone pairs of electrons on the O atom placed? - What orbital is the lone pair of electrons on the N atom placed? - What type of bond(s) are formed between Ca1 – C? - What type of bond(s) are formed between C = O? - What type of bond(s) are formed between C – N? - What type of bond(s) are formed between N – Ca2? - What type of bond(s) are formed between N – H? - What is the angle between Ca1 – C = O? - What is the angle between Ca1 – C – N? - What is the angle between O = C – N? - What is the angle between C – N – Ca2?
8. Compute for the formal charge (FC) on each atom in the following compounds. a. H3N - BH3 b. [H2CNH2]+ c. H3O+ d. HCO3- 9. Draw Lewis structures for the following compounds, showing an appropriate formal charges. a. [CH3OH2]+ b. [HONH3]+ c. NaBH3CN d. CH3NH3+ 10. For each of the following compounds, draw the important resonance forms. Indicate which structures are major and minor contributors or whether they would have the same energy. a. [CH3OCH2]+ b. H2SO4 c. CO3-2 d. H2C=CH-+CH2 e. [CH3C(OCH3)2 ]+ 11. Draw the complete Lewis structures for the following condensed structural formulas. a. CH3(CH2)3CH(CH3)2
8. Compute for the formal charge (FC) on each atom in the following compounds. a. H3N - BH3 b. [H2CNH2]+ c. H3O+ d. HCO3- 9. Draw Lewis structures for the following compounds, showing an appropriate formal charges. a. [CH3OH2]+ b. [HONH3]+ c. NaBH3CN d. CH3NH3+ 10. For each of the following compounds, draw the important resonance forms. Indicate which structures are major and minor contributors or whether they would have the same energy. a. [CH3OCH2]+ b. H2SO4 c. CO3-2 d. H2C=CH-+CH2 e. [CH3C(OCH3)2 ]+ 11. Draw the complete Lewis structures for the following condensed structural formulas. a. CH3(CH2)3CH(CH3)2 b. CH3CH2COCN c. (CH3)3CCOCHCH2 d. (CH3CH2)2CO e. (CH3)2CHCH2Cl 12. Draw the line-angle formula for the following condensed structural formulas. a. CH3(CH2)3CH(CH3)2 b. CH3CH2COCN c. (CH3)3CCOCHCH2 d. (CH3CH2)2CO e. (CH3)2CHCH2Cl
C(s) → C(g), ΔH = +715 kJmol-1 Cl2(g) → 2Cl(g), ΔH = +242 kJmol-1 C(s) + 2Cl2(g) → CCl4(g), ΔH = -135.5 kJmol-1 Calculate the average bond dissociation enthalpy of a C-Cl bond.
1. Conjugated radicals, ions, or molecules are more stable than non-conjugated ones, why? 2. Charge separation decreases stability, why? 3. Structures in which all of the atoms have a complete valence shell of electrons are especially stable and make large contributions to the hybrid, why?
Use the table below to determine ΔH for the following reactionN 2H 4(g) + H 2O(g) ↔ NH 2OH(g) + NH 3(g) Bond Energies, kJ/mol Single Bonds H C N O S F Cl Br I H 432 C 411 346 N 386 305 167 O 459 358 201 142 S 363 272 --- --- 286 F 565 485 283 190 284 155 Cl 428 327 313 218 255 249 240 Br 362 285 243 201 217 249 216 190 I 295 213 --- 201 --- 278 208 175 149 Multiple Bonds C=C 602 C=N 615 C=O 799 C≡C 835 C≡N 887 C≡O 1072 N=N 418 N=O 607 S=O (in SO2) 532 N≡N 942 O2 494 S=O (in SO3) 469
Use bond dissociation enthalpies to calculate values of delta H° for the following reactions a) CH3-CH3 + I2 = CH3CH2I + HI b) CH3CH2Cl + HI = CH3CH2I + HCl
Some bond dissociation energies in kJ/mol are listed. 1°, 2°, 3° means primary, secondary,tertiary.1° C-H 423 2° C-H 413 3° C-H 4041° C-CN 509 2° C-CN 506 3° C-CN 493For the hypothetical reaction below, do two things:1) Estimate the enthalpy change ΔH° for the reaction. Show your work in the space below.2) Draw a circle around the molecule with the lower enthalpy.
SO < SO2< SO32-( a) Match each species with the number of covalent bonds predicted by Lewis structures to exist between an S atom and an O atom bonded to this S atom. (Hint: Average the number of bonds between S and an attached oxygen atom in a particular position using all of your resonance structures for the species that you are working on.)SO32- : is it 1.00, 1.33, 1.50, 2.00, 3.00 (b) Match each species with the correct formal charge on the central S atom. SO32- : is it -1.00 , -0.67 , -0.50, 0.00, +1.00, or +2.00 ? (c) Match each species with the average formal charge on an outside oxygen atom predicted by Lewis structures. SO32- : is it -1.00 , -0.67 , -0.50, 0.00, +1.00, or +2.00 ?
The H-N-H bond angle in NH3 is not what would be expected using VSEPR (a usefultool) without adding some rules about lone pairs being more repulsive than bond pairs(??).Explain (with diagrams if helpful) why the bond angle is 107° and not 109o according to this treatment.
Likeseveralotherbonds,carbon-oxygenbondshavelengthsthatdependon bond order. Draw Lewis structures for the following species, and arrange them in order of increasing bond length. a) CO b) H2CO c) CH3OH d) CO32- e) HCO3-Hint for (e): which atom will the H be attached to? Note that HCO3- is formed +2- 2-when you add an H to CO3 . Looking at your structure for CO3 , where does it make the most sense to add the H+?

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