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Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485

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BuyFindarrow_forward

Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485
Chapter 7.SE, Problem 23VC
Textbook Problem
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Assign E or Z stereochemistry to the double bonds in each of the following alkenes, and convert each drawing into a skeletal structure (red = O, green = Cl):

Chapter 7.SE, Problem 23VC, Assign E or Z stereochemistry to the double bonds in each of the following alkenes, and convert each

Interpretation Introduction

a)

Organic Chemistry, Chapter 7.SE, Problem 23VC , additional homework tip  1

Interpretation:

The skeletal structure of the compound given in the model is to be drawn and the stereochemistry of the double bond to be assigned as E or Z.

Concept introduction:

The isomer that has the higher ranked groups on each carbon on the same side of the double bond is said to have Z configuration. If the higher ranked groups are on the opposite sides, the alkene is said to have E configuration.

In skeletal structures the carbon and hydrogen atoms are not usually shown. Instead carbon atoms are assumed to be at each intersection of two lines and at the end of each line. Hydrogen atoms required are fitted mentally having in mind the valence of carbon is four. Atoms other than carbon and hydrogen are shown.

To draw:

The skeletal structure of the compound given in the model and to assign the stereochemistry of the double bond as E or Z.

Explanation of Solution

The carbon in the left side of the double bond is attached to Cl and CH3. Among these two Cl ranks higher as it has high atomic number. The carbon in the right side of the double bond is attached to CHO and CH(CH3)2. Among these two the carbon in CHO is attached to H, O, O(double bond)...

Interpretation Introduction

b)

Organic Chemistry, Chapter 7.SE, Problem 23VC , additional homework tip  2

Interpretation:

The skeletal structure of the compound given in the model is to be drawn and the stereochemistry of the double bond to be assigned as E or Z.

Concept introduction:

The isomer that has the higher ranked groups on each carbon on the same side of the double bond is said to have Z configuration. If the higher ranked groups are on the opposite sides, the alkene is said to have E configuration.

In skeletal structures the carbon and hydrogen atoms are not usually shown. Instead carbon atoms are assumed to be at each intersection of two lines and at the end of each line. Hydrogen atoms required are fitted mentally having in mind the valence of carbon is four. Atoms other than carbon and hydrogen are shown.

To draw:

The skeletal structure of the compound given in the model and to assign the stereochemistry of the double bond as E or Z.

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Chapter 7 Solutions

Organic Chemistry
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Ch. 7.5 - Which member in each of the following sets ranks...Ch. 7.5 - Rank the substituents in each of the following...Ch. 7.5 - Assign E or Z configuration to the following...Ch. 7.5 - Assign stereochemistry (E or Z) to the double bond...Ch. 7.6 - Name the following alkenes, and tell which...Ch. 7.8 - Predict the products of the following reactions:Ch. 7.8 - What alkenes would you start with to prepare the...Ch. 7.9 - Show the structures of the carbocation...Ch. 7.9 - Draw a skeletal structure of the following...Ch. 7.11 - On treatment with HBr, vinylcyclohexane undergoes...Ch. 7.SE - Name the following alkenes, and convert each...Ch. 7.SE - Assign E or Z stereochemistry to the double bonds...Ch. 7.SE - The following carbocation is an intermediate in...Ch. 7.SE - The following alkyl bromide can be made by HBr...Ch. 7.SE - Predict the major product and show the complete...Ch. 7.SE - Each electrophilic addition reaction below...Ch. 7.SE - When 1, 3-butadiene reacts with one mole of HBr,...Ch. 7.SE - When methyl vinyl ether reacts with a strong acid,...Ch. 7.SE - Addition of HCl to 1-isopropylcyclohexene yields a...Ch. 7.SE - Addition of HCl to...Ch. 7.SE - Limonene, a fragrant hydrocarbon found in lemons...Ch. 7.SE - epi-Aristolochene, a hydrocarbon found in both...Ch. 7.SE - Calculate the degree of unsaturation in the...Ch. 7.SE - How many hydrogens does each of the following...Ch. 7.SE - Loratadine, marketed as an antiallergy medication...Ch. 7.SE - Name the following alkenes:Ch. 7.SE - Draw structures corresponding to the following...Ch. 7.SE - Name the following cycloalkenes:Ch. 7.SE - Ocimene is a triene found in the essential oils of...Ch. 7.SE - α-Farnesene is a constituent of the natural wax...Ch. 7.SE - Menthene, a hydrocarbon found in mint plants, has...Ch. 7.SE - Draw and name the six alkene isomers, C5H10,...Ch. 7.SE - Draw and name the 17 alkene isomers, C6H12,...Ch. 7.SE - Rank the following sets of substituents according...Ch. 7.SE - Assign E or Z configuration to each of the...Ch. 7.SE - Which of the following E, Z designations are...Ch. 7.SE - Rank the double bonds below in terms of increasing...Ch. 7.SE - trans-2-Butene is more stable than cis-2-butene by...Ch. 7.SE - Cyclodecene can exist in both cis and trans forms,...Ch. 7.SE - Normally, a trans alkene is more stable than its...Ch. 7.SE - trans-Cyclooctene is less stable than...Ch. 7.SE - Tamoxifen, a drug used in the treatment of breast...Ch. 7.SE - Rank the carbocations below in terms of increasing...Ch. 7.SE - Use Hammond’s Postulate to determine which...Ch. 7.SE - Carbocations can be stabilized by resonance. Draw...Ch. 7.SE - Predict the major product in each of the following...Ch. 7.SE - Predict the major product from addition of HBr to...Ch. 7.SE - Alkenes can be converted into alcohols by...Ch. 7.SE - Each of the following carbocations can rearrange...Ch. 7.SE - Allene (1,2-propadiene), H2C=C=CH2, has two...Ch. 7.SE - The heat of hydrogenation for allene (Problem...Ch. 7.SE - Retin A, or retinoic acid, is a medication...Ch. 7.SE - Fucoserratene and ectocarpene are sex pheromones...Ch. 7.SE - tert-Butyl esters [RC02C(CH3)3] are converted into...Ch. 7.SE - Vinylcyclopropane reacts with HBr to yield a...Ch. 7.SE - Calculate the degree of unsaturation in each of...Ch. 7.SE - The isobutyl cation spontaneously rearranges to...Ch. 7.SE - Draw an energy diagram for the addition of HBr to...Ch. 7.SE - Sketch the transition-state structures involved in...Ch. 7.SE - Aromatic compounds such as benzene react with...Ch. 7.SE - Reaction of 2, 3-dimethyl-l-butene with HBr leads...

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