Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 14.SE, Problem 48AP
The following ultraviolet absorption maxima have been measured:
1,3-Butadiene 217 nm
2-Methyl-1,3-butadiene 220 nm
1,3-Pentadiene 223 nm
2,3-Dimethyl-1,3-butadiene 226 nm
2,4-Hexadiene 227 nm
2,4-Dimethyl-1,3-pentadiene 232 nm
2,5-Dimethyl-2,4-hexadiene 240 nm
What conclusion can you draw about the effect of alkyl substitution on UV absorption maxima? Approximately what effect does each added alkyl group have?
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The Diels-Alder reaction between butadiene and dimethyl maleate yields a ring structure, as shown in the product. Complete
the structure by drawing any missing bonds and indicating the stereochemistry of the new stereocenters.
Select
Draw
Rings
More
Erase
C
160 °C
+
24h
Name the following compound:
Br
O (1S, 3S,4R)-1-chloro-3-bromo-4-isopropylcyclohexane
O (1R, 2R, 5R)-1-bromo-2-isopropyl-5-chlorocyclohexane
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O (15, 25, 5R)-1-bromo-2-isopropyl-5-chlorocyclohexane
Which of the following compounds does NOT absorb in the UV-visible range (200 - 900 nm)?
Select one:
Phenol
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Benzene
Chapter 14 Solutions
Organic Chemistry
Ch. 14.1 - Prob. 1PCh. 14.2 - Give the structures of both 1, 2 and 1, 4 adducts...Ch. 14.2 - Prob. 3PCh. 14.2 - Give the structures of both 1, 2 and 1, 4 adducts...Ch. 14.3 - Prob. 5PCh. 14.3 - Prob. 6PCh. 14.5 - Predict the product of the following Diels–Alder...Ch. 14.5 - Prob. 8PCh. 14.5 - Which of the following dienes have an s-cis...Ch. 14.5 - Predict the product of the following Diels–Alder...
Ch. 14.6 - Prob. 11PCh. 14.6 - Prob. 12PCh. 14.7 - Prob. 13PCh. 14.7 - Prob. 14PCh. 14.8 - Which of the following compounds would you expect...Ch. 14.SE - Prob. 16VCCh. 14.SE - Show the product of the Diels–Alder reaction of...Ch. 14.SE - Prob. 18VCCh. 14.SE - Prob. 19VCCh. 14.SE - Prob. 20MPCh. 14.SE - Prob. 21MPCh. 14.SE - In light of your answer to Problem 14-21 propose...Ch. 14.SE - Luminol, which is used by forensic scientists to...Ch. 14.SE - Prob. 24MPCh. 14.SE - Give IUPAC names for the following compounds:Ch. 14.SE - Prob. 26APCh. 14.SE - Prob. 27APCh. 14.SE - Electrophilic addition of Br2 to isoprene...Ch. 14.SE - Prob. 29APCh. 14.SE - Prob. 30APCh. 14.SE - Predict the products of the following...Ch. 14.SE - 2,3-Di-tert-butyl-1,3-butadiene does not undergo...Ch. 14.SE - Prob. 33APCh. 14.SE - Prob. 34APCh. 14.SE - Prob. 35APCh. 14.SE - Prob. 36APCh. 14.SE - Rank the following dienophiles in order of their...Ch. 14.SE - Prob. 38APCh. 14.SE - Prob. 39APCh. 14.SE - Prob. 40APCh. 14.SE - Although the Diels–Alder reaction generally...Ch. 14.SE - Prob. 42APCh. 14.SE - Tires whose sidewalls are made of natural rubber...Ch. 14.SE - Prob. 44APCh. 14.SE - Prob. 45APCh. 14.SE - Prob. 46APCh. 14.SE - Would you expect allene, H2C = C = CH2, to show a...Ch. 14.SE - The following ultraviolet absorption maxima have...Ch. 14.SE - Prob. 49APCh. 14.SE - -Ocimene is a pleasant-smelling hydrocarbon found...Ch. 14.SE - Draw the resonance forms that result when the...Ch. 14.SE - Prob. 52APCh. 14.SE - Treatment of 3,4-dibromohexane with strong base...Ch. 14.SE - Prob. 54APCh. 14.SE - Prob. 55APCh. 14.SE - Prob. 56APCh. 14.SE - Prob. 57APCh. 14.SE - Prob. 58APCh. 14.SE - Hydrocarbon A, C10H14, has a UV absorption at...Ch. 14.SE - Prob. 60APCh. 14.SE - Prob. 61APCh. 14.SE - Prob. 62APCh. 14.SE - Prob. 63APCh. 14.SE - Prob. 64APCh. 14.SE - The double bond of an enamine (alkene + amine) is...Ch. 14.SE - Prob. 66AP
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- 12-47 Draw a structural formula for an alkene with the molecular formula C5H10that reacts with Br2to give each product. ch3 I (a) ch3c—chch3Br Br (c) CH2CHCH2CH2CH3Br Brarrow_forwardSeveral diamines are building blocks for the synthesis of pharmaceuticals and agro- chemicals. Show how both 1,3-propanediamine and 1,4-butanediamine can be pre- pared from acrylonitrile. NH2 H,N `NH2 H,N CH,=CH-C=N 1,3-Propanediamine 1,4-Butanediamine Acrylonitrilearrow_forwardShow how 5-methyl-1,3-cyclopentadiene rearranges to form 1-methyl-1,3-cyclopentadiene and 2-methyl1,3-cyclopentadiene.arrow_forward
- 4 what is the ftir interpretation of 1-chloro-1-methylcyclohexane?arrow_forwardThe boiling point of methylcyclohexane (C7H14, MW 98.2) is 101°C. The boiling point of perfluoromethylcyclohexane (C7F14, MW 350) is 76°C. Account for the fact that although the molecular weight of perfluoromethylcyclohexane is over three times that of methylcyclohexane, its boiling point is lower than that of methylcyclohexane.arrow_forwardWhat are the safety hazards of these chemicals? Biphenyl (92-52-4) bromine (7726-95-6) hydrogen bromide (10035-10-6) 4,4'-DIBROMOBIPHENYL,Biphenyl, 4,4'-dibromo- (92-86-4) Benzene (71-43-2)arrow_forward
- Cyclobutane reacts with bromine to give bromocyclobutane, but bicyclobutane reacts with bromine to give 1,3-dibromocyclobutane. Account for the differences between the reactions of these two compounds. heat + Br2 -Br + HBr Cyclobutane Bromocyclobutane heat Br2 Br Br Bicyclobutane 1,3-Dibromocyclobutanearrow_forwardHil H H C6H5-C-C-C6H5 C6H5 + HCI C6H5 H. ÓH ČI This equation shows the reaction of trans-2,3-diphenyloxirane with hydrogen chloride to form 2-chloro-1,2-diphenylethanol. How many total stereoisomers are possible for 2-chloro-1,2-diphenylethanol? 4 Given that opening of the epoxide ring in this reaction is stereoselective, provide the names of the only two isomeric products formed using IUPAC guidelines. product 1: (1R 2R) product 2: ((1S 2S) v 2-chloro-1,2-diphenylethanol 2-chloro-1,2-diphenylethanol Try Another Version 1 item attempt remaining Submit Answerarrow_forwardThe Diels-Alder reaction between butadiene and dimethyl maleate yields a ring structure, as shown in the product. Complete the structure by drawing any missing bonds and indicating the stereochemistry of the new stereocenters. Select Draw Rings More Erase H 160 °C 24h Harrow_forward
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