ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 27, Problem 27.2P
For each molecular orbital in Figure 27.2, count the number of bonding interactions (interactions between adjacent orbitals of similar phase) and the number of nodes. (a) How do these two values compare for a bonding molecular orbital? (b) How do these two values compare for an antibonding molecular orbital?
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1) In electron sea model, all the electrons of the contributing atoms are delocalized in the array of metal atoms and are involved in metallic bonding.
2) In molecular orbital theory, the no. of molecular orbitals formed is twice the no. of atomic orbitals used in the formation of the molecular orbitals.
3) Resonance structures of the same compound can have different arrangement of atoms.
Draw a picture that shows all three 2p orbitals on one atomand all three 2p orbitals on another atom. (a) Imagine theatoms coming close together to bond. How many σ bondscan the two sets of 2p orbitals make with each other? (b) Howmany π bonds can the two sets of 2p orbitals make with eachother? (c) How many antibonding orbitals, and of what type,can be made from the two sets of 2p orbitals?
Identify and label geometry, hybridization, sigma bonds and pi bonds for any atom/group of atoms.
A structure of XanaxTM is shown here.
(a) and (b): Identify the hybridization state AND geometry of each of the indicated atoms.
(c) List the total number of pi bonds in the structure.
(d) List the total number of tetrahedral carbons.
CI
N
(a)
(b)
Chapter 27 Solutions
ORGANIC CHEMISTRY
Ch. 27 - Prob. 27.1PCh. 27 - Problem 27.2
For each molecular orbital in Figure...Ch. 27 - Problem 27.3
(a) Using Figure 27.2 as a guide,...Ch. 27 - Problem 27.4
(a) How many molecular orbitals are...Ch. 27 - Prob. 27.5PCh. 27 - Prob. 27.6PCh. 27 - Prob. 27.7PCh. 27 - Prob. 27.8PCh. 27 - Prob. 27.9PCh. 27 - Prob. 27.10P
Ch. 27 - Problem 27.11
What product would be formed by the...Ch. 27 - Consider cycloheptatrienone and ethylene, and draw...Ch. 27 - Problem 27.13
Show that a thermal suprafacial...Ch. 27 - Prob. 27.14PCh. 27 - a Draw the product of the following [4+2]...Ch. 27 - Prob. 27.16PCh. 27 - Prob. 27.17PCh. 27 - Problem 27.18
Using orbital symmetry, explain why...Ch. 27 - Prob. 27.19PCh. 27 - Prob. 27.20PCh. 27 - Prob. 27.21PCh. 27 - Prob. 27.22PCh. 27 - Prob. 27.23PCh. 27 - Prob. 27.24PCh. 27 - Problem 27.25
(a) What product is formed by the...Ch. 27 - Prob. 27.26PCh. 27 - Prob. 27.27PCh. 27 - Prob. 27.28PCh. 27 - Prob. 27.29PCh. 27 - Prob. 27.30PCh. 27 - Prob. 27.31PCh. 27 - Prob. 27.32PCh. 27 - Prob. 27.33PCh. 27 - Prob. 27.34PCh. 27 - Prob. 27.35PCh. 27 - Prob. 27.36PCh. 27 - Prob. 27.37PCh. 27 - Prob. 27.38PCh. 27 - Prob. 27.39PCh. 27 - Prob. 27.40PCh. 27 - 27.41 What starting materials are needed to...Ch. 27 - Prob. 27.42PCh. 27 - Prob. 27.43PCh. 27 - Prob. 27.44PCh. 27 - Prob. 27.45PCh. 27 - Prob. 27.46PCh. 27 - 27.47 What product is formed from the [5,5]...Ch. 27 - Prob. 27.48PCh. 27 - 27.49 Draw structures for A, B, and C in the...Ch. 27 - Prob. 27.50PCh. 27 - Prob. 27.51PCh. 27 - 27.52 Draw the products of each reaction.
c....Ch. 27 - Prob. 27.53PCh. 27 - 27.54 Draw a stepwise, detailed mechanism for the...Ch. 27 - Prob. 27.55PCh. 27 - Prob. 27.56PCh. 27 - Prob. 27.57PCh. 27 - 27.58 Draw a stepwise, detailed mechanism for the...Ch. 27 - Prob. 27.59PCh. 27 - Prob. 27.60PCh. 27 - Prob. 27.61PCh. 27 - Prob. 27.62PCh. 27 - Prob. 27.63P
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- Indicate whether each statement is true or false. (a) s orbitalscan only make s or s* molecular orbitals. (b) The probabilityis 100% for finding an electron at the nucleus in a p* orbital.(c) Antibonding orbitals are higher in energy than bondingorbitals (if all orbitals are created from the same atomic orbitals).(d) Electrons cannot occupy an antibonding orbital.arrow_forward(a) Determine the molecular geometry of SeF4using the VSEPR model. The molecular geometry of SeF4 is (___________________) linear or trigonal planar or bent tetrahedral or trigonal pyramidal or trigonal bipyramidal or seesaw or T-shaped or octahedral or square pyramidal or square planar . (b) Explain why the molecular geometry of SeF4 is different from that of IBr3, although they have similar electron-domain geometries. Although both SeF4 and IBr3 have the electron-domain geometry of (_________________) linear or trigonal planar or bent tetrahedral or trigonal pyramidal or trigonal bipyramidal or seesaw or T-shaped or octahedral or square pyramidal or square planar, IBr3 has _____ lone pair(s) of electrons whereas SeF4 has only ________ lone electron pair(s) in the (______________) axial or equatorial positions. Accordingly, the molecular geometry of SeF4 is (________________) linear or trigonal planar or bent tetrahedral or trigonal pyramidal or trigonal bipyramidal or seesaw or…arrow_forwardFor each statement, indicate whether it is true or false. (a) The greater the orbital overlap in a bond, the weaker the bond. [b] The greater the orbital overlap in a bond, the shorter the bond. [c] To create a hybrid orbital, you could use the s orbital on one atom with a p orbital on another atom. [d] Nonbonding electron pairs cannot occupy a hybrid orbital.arrow_forward
- (a) If you combine two atomic orbitals on two different atomsto make a new orbital, is this a hybrid orbital or a molecularorbital? (b) If you combine two atomic orbitals onone atom to make a new orbital, is this a hybrid orbital or amolecular orbital? (c) Does the Pauli exclusion principle apply to MOs? Explain.arrow_forwardThis question will explore bonding in OH and OH- using molecular orbital theory a) Explain any differences in energy between atomic orbitals of O vs. the atomic orbital of H. b) Taking into account your response to part a, draw a molecular orbital diagram for the valence electrons in the neutral diatomic OH. Include a sketch of the molecular orbitals in your sketch. The relevant molecular orbitals listed in order of increasing energy are σ2s(1 orbital), σ2p(1 orbital), π2p (2 orbitals), σ2p∗(1 orbital). (Hint: the 2s atomic orbital of the O atom to not interact with the 1s atomic orbitals on the H atom). c) How do you expect the bond length in OH to compare to that of the OH- anion? Justify your answer by calculating the bond order of each species.arrow_forwardThe molecule shown below is called furan. It is represented intypical shorthand way for organic molecules, with hydrogenatoms not shown, and each of the 4 vertices representing acarbon atom.(a) What is the molecular formula for furan? (b) How manyvalence electrons are there in the molecule? (c) What isthe hybridization at each of the carbon atoms? (d) Howmany electrons are in the p system of the molecule? (e) TheC¬C¬C bond angles in furan are much smaller than thosein benzene. The likely reason is which of the following: (i) Thehybridization of the carbon atoms in furan is different fromthat in benzene, (ii) Furan does not have another resonancestructure equivalent to the one above, or (iii) The atoms in afive-membered ring are forced to adopt smaller angles than ina six-membered ring.arrow_forward
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