Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 27, Problem 27.3P
(a) Using Figure 27.2 as a guide, draw the molecular orbitals for hexa
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14.How many electrons are present in the nonbonding π molecular orbital of the allyl anion?A)0B)1C)2D)3E)4
15.Which of the following statements concerning electrocyclic reactions is correct?A)The ground state HOMO of a compound with an even number of conjugated double bonds is asymmetric.B)The allowed mode of ring closure under thermal conditions for a molecule containing an even number of conjugated double bonds is disrotatory.C)The allowed mode of ring closure under photochemical conditions for a molecule containing an odd number of conjugated double bonds is disrotatory.D)both B and CE)none of the above
16.Under thermal conditions,(2E,4Z)-hexadiene undergoes a ___ ring closure to yield ___.A)conrotatory,cis-3,4-dimethylcyclobuteneB)conrotatory,trans-3,4-dimethylcyclobuteneC)disrotatory,cis-3,4-dimethylcyclobuteneD)disrotatory,trans-3,4-dimethylcyclobutene
17.Under photochemical conditions,(2E,4Z)-hexadiene undergoes a ___ ring closure to yield…
Consider the reaction between (1S,3S)‑1‑chloro‑3‑methylcyclopentane and methanethiol in the presence of sodium hydroxide.
(a) Draw the organic product and clearly indicate stereochemistry by showing the hydrogen on the chirality centers and using wedge and dash bonds.
(b) Then analyze the stereochemistry of the product.
racemic
chiral
achiral
(1R, 3S)
(1R, 3R)
(1S, 3S)
(b)
(d)
CH3
CH3CHCH₂CH₂CH₂Br
SCH₂CH3
1.
(NH₂)₂C=S
2. NaOH, H₂O
H₂O2, H₂O, ?
?
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 - Problem 27.25
(a) What product is formed by the...Ch. 27 - Prob. 27.25PCh. 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 - Prob. 27.41PCh. 27 - Prob. 27.42PCh. 27 - Prob. 27.43PCh. 27 - Prob. 27.44PCh. 27 - Prob. 27.45PCh. 27 - 27.47 What product is formed from the [5,5]...Ch. 27 - 27.49 Draw structures for A, B, and C in the...Ch. 27 - Prob. 27.48PCh. 27 - Prob. 27.49PCh. 27 - 27.52 Draw the products of each reaction.
c....Ch. 27 - Prob. 27.51PCh. 27 - 27.54 Draw a stepwise, detailed mechanism for the...Ch. 27 - Prob. 27.53PCh. 27 - Prob. 27.54PCh. 27 - 27.58 Draw a stepwise, detailed mechanism for the...Ch. 27 - Prob. 27.56PCh. 27 - Prob. 27.57PCh. 27 - Prob. 27.58PCh. 27 - Prob. 27.59P
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- (C) Provide the starting materials (diene and dienophile) necessary to form the ind product through a Diels-Alder reaction (beware of the stereochemical information). (a) (b) (c) (d) - Diene - Dienophile- Diene Dienophile - Diene + Dienophile- -Diene Dienophile- A Dor Br Br A ✓ CO₂Me CO₂Me A 4 A MeO CNarrow_forwardHere is the visible absorbance spectrum and electromagnetic spectrum. 1. Determine which molecule (a,b,c, or d) has the smaller HOMO-LUMO gap. Briefly explainyour reasoning. rememeber more conjugation is a smaller gap.arrow_forwardPropose at least three methods to convert CgHsCH,CH,Br to CęH;CH,CH3.arrow_forward
- Draw structural formulas for the following compounds (a) (2Z,4Z)-2,4-dibromo-3-methylhepta-2,4-diene (b) ((2E,4Z)-2-bromo-3,5-dichloro-4-methylhexa-2,4-dienearrow_forwardThere is a diene of molecular formula C5H8 that is chiral. Draw its structure.arrow_forwardUse a sheet of paper and draw structures for all the isolated, conjugated, and cumulated dienes of molecular formula C5Hg.arrow_forward
- The degree of unsaturation, or index of hydrogen deficiency, is the number of pi bonds plus rings in a molecule. Specify the degree of unsaturation (index of hydrogen deficiency) of the following formulas: (a) C24H24 (b) C8H1002 (c) CgH8N₂arrow_forward(b) مله + But-3-en-2-one NaOEtarrow_forwardExplain [3,3] Sigmatropic Rearrangements ?arrow_forward
- • Q: Calculate the wavelength of the radiation that will be absorbed in promoting an electron from the HOMO to the LUMO in butadiene.arrow_forwardConstruct an MO energy diagram for the cycloheptatrienyl cation and describe its ground-state electron configurationarrow_forwardThe degree of unsaturation, or index of hydrogen deficiency, is the number of pi bonds plus rings in a molecule.Specify the degree of unsaturation (index of hydrogen deficiency) of the following formulas:(a) C9H12(b) C14H18(c) C10H8N2arrow_forward
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