Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 9, Problem 8CTQ
Interpretation Introduction
Interpretation: The product for the given reaction should be predicted.
Concept introduction:
The reaction of an
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The ratio between the products resulting from the reversible Diels-Alder reaction of furan and N-
phenyl maleimide can be tuned by varying the reaction temperature and solvent. Please answer
the following questions.
A) Draw the products of this reaction that agree with the product ratios at each temperature when
run either neat or in ether. Label each product as either endo or exo and be sure to indicate
stereochemistry.
Q
furan n-phenyl maleimide
+
Time
7 days
7 days
20 days
7 days
then 5 h
Temp
0 °C
ambient
ambient
0 °C
60 °C
A B
36
49
48
41
68a 23a
43
21
A
+
N-phenyl-
maleimide
(%)
14
11
ga
36
B) Draw the reaction coordinate diagram of this reaction. Label the products from part A, and
provide a drawing of any transition states.
B
Provide specific examples/reaction scheme/mechanism for each of the following:
a) Hoffman elimination
b) Wittig reaction
c) Zaitsev's rule
d) Anti-Markovnikov's rule
e) Stereoelectronic effect
Given three equally branched structures and with only a difference in the type of group attached to each (OH, NH3, or OTs), which compound would react faster in an SN1 reaction?
Chapter 9 Solutions
Organic Chemistry: A Guided Inquiry
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- Complete the following reactions. Where more than one product is possible, show only the one expected according to Markovnikovs rule. a. b.CH3CH2CH=CH2+Cl2 c. d.arrow_forwardWhat is more nucleophilic CH3O- or CH3S- ? The solvent isn't mentioned, or it can be assumed it's aprotic if needed, or in other words it doesn't interfere with nucleophilicity.arrow_forwardFor the given molecule, highlight any nucleophilic sites in red and any electrophilic sites in blue. O: 439 0-Harrow_forward
- How do you properly write an SN1 reaction, with transition states/intermediate steps included?arrow_forwardFluoride ion is usually a poor leaving group because it is not very polarizable. Fluorideserves as the leaving group in the Sanger reagent (2,4-dinitrofluorobenzene), used inthe determination of peptide structures (Chapter 24). Explain why fluoride works as aleaving group in this nucleophilic aromatic substitution, even though it is a poor leavinggroup in the SN1 and SN2 mechanisms.arrow_forwardMoecules with larger amounts of electron delocalization will have blank HOMO/LUMO gaps.arrow_forward
- Here is the same figure as in the previous two questions, but omitting the red circles. Cys157 Cys157 Cys157 His296 His296 His296 LOH HN HN HN N? -CO2 CH2 Asn329 Asn329 Asn329- Cys157 His296 LOH HN H HyC. Asn329 Which of the following roles is played by the imidazole side chain of His296? Pick the one best [ Select ] answer.arrow_forwardWhat is the major product a or b.arrow_forwardIn electrophilic aromatic substitution, a group attached to the aromatic ring does not affect ring reactivity. Is that true or false?arrow_forward
- A problem in dyeing fabrics is the degree of fastness of the dye to the fabric. Many of the early dyes were surface dyes; that is, they did not bond to the fabric, with the result that they tended to wash off after repeated laundering. Indigo, for example, which gives the blue color to blue jeans, is a surface dye. Color fastness can be obtained by bonding a dye to the fabric. The first such dyes were the so-called reactive dyes, developed in the 1930s for covalently bonding dyes containing-NH, groups to cotton, wool, and silk fabrics. In the first stage of the first-developed method for reactive dyeing, the dye is treated with cyanuric chloride, which links to the fabric through the amino group of the dye. The remaining chlorines are then displaced by the-OH groups of cotton (cellulose) or the-NH, groups of wool or silk (both proteins). CI -Cotton Dye-NH, Но-Сotton N' CI CI Dye-NH CI Dye-NH 'N. 0-Cotton Cyanuric chloride A reactive dye Dye covalently bonded to cotton Propose a…arrow_forwardKk.82.arrow_forwardIn the E2 reaction of 2-bromopentane with sodium tert-butoxide, 1-pentene is favored over 2- pentene. It is based on O the size of base used. O the Zaisev's rule. O the strength of the base used. O the Hoffman product. O the stability of alkenearrow_forward
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