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Concept explainers
(a)
Interpretation:
The mechanism for the reaction that will take place when the given compound is treated with
Concept introduction:
Diazomethane,
The stereochemistry of the double bond is preserved in the addition. If the double bond has a cis relationship, then the two substituents end up on the same side of the cyclopropane ring. If the two substituents on the double bond are trans to each other, they end up on the opposite sides of the cyclopropane ring. This also determines the product distribution if the cyclic product is chiral. If the starting
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Answer to Problem 12.26P
The mechanism for the reaction when
Explanation of Solution
Diazomethane dissociates heterolytically when irradiated with ultraviolet light to produce a carbene and a nitrogen molecule.
The carbene then simultaneously adds to the initially double-bonded carbons. The lone pair on the carbene forms a bond with one carbon while the
Since the starting alkene is chiral, the product will be a mixture of two enantiomers. The pair of enantiomers is produced because the carbene can add either above or below the plane of the ring in the reactant.
Thus the complete mechanism for this reaction can be drawn as
A carbene adds to an alkene or
(b)
Interpretation:
The mechanism for the reaction that will take place when the given compound is treated with
Concept introduction:
Diazomethane,
The stereochemistry of the double bond is preserved in the addition. If the double bond has a cis relationship, then the two substituents end up on the same side of the cyclopropane ring. If the two substituents on the double bond are trans to each other, they end up on the opposite sides of the cyclopropane ring. This also determines the product distribution if the cyclic product is chiral. If the starting alkene is achiral and the product chiral, the product is a racemic mixture of enantiomers. If the starting alkene is also chiral, then an unequal mixture of enantiomers is produced.
![Check Mark](/static/check-mark.png)
Answer to Problem 12.26P
The mechanism for the given reaction is
Explanation of Solution
Diazomethane dissociates heterolytically when irradiated with ultraviolet light to produce a carbene and a nitrogen molecule.
The carbene then simultaneously adds to the initially double-bonded carbons. The lone pair on the carbene forms a bond with one carbon while the
The carbene then simultaneously adds to the initially double-bonded carbons. The lone pair on the carbene forms a bond with one carbon while the
Since the starting alkene is chiral, the product will be a mixture of two enantiomers. The pair of enantiomers is produced because the carbene can add either above or below the plane of the ring in the reactant.
Thus the complete mechanism for this reaction can be drawn as:
A carbene adds to an alkene or alkyne to produce a cyclopropane ring.
(c)
Interpretation:
The mechanism for the reaction that will take place when the given compound is treated with
Concept introduction:
Diazomethane,
The stereochemistry of the double bond is preserved in the addition. If the double bond has a cis relationship, then the two substituents end up on the same side of the cyclopropane ring. If the two substituents on the double bond are trans to each other, they end up on the opposite sides of the cyclopropane ring. This also determines the product distribution if the cyclic product is chiral. If the starting alkene is achiral and the product chiral, the product is a racemic mixture of enantiomers. If the starting alkene is also chiral, then an unequal mixture of enantiomers is produced.
![Check Mark](/static/check-mark.png)
Answer to Problem 12.26P
The mechanism for the given reaction is
Explanation of Solution
Diazomethane dissociates heterolytically when irradiated with ultraviolet light to produce a carbene and a nitrogen molecule.
The carbene then simultaneously adds to the initially double-bonded carbons. The lone pair on the carbene forms a bond with one carbon while the
Only one product is formed in this case because of the symmetry of the reactant alkene about the axis of the double bond.
Thus, the complete mechanism for the given reaction can be drawn as
A carbene adds to an alkene or alkyne to produce a cyclopropane ring.
(d)
Interpretation:
The mechanism for the reaction that will take place when the given compound is treated with
Concept introduction:
Diazomethane,
The stereochemistry of the double bond is preserved in the addition. If the double bond has a cis relationship, then the two substituents end up on the same side of the cyclopropane ring. If the two substituents on the double bond are trans to each other, they end up on the opposite sides of the cyclopropane ring. This also determines the product distribution if the cyclic product is chiral. If the starting alkene is achiral and the product chiral, the product is a racemic mixture of enantiomers. If the starting alkene is also chiral, then an unequal mixture of enantiomers is produced.
![Check Mark](/static/check-mark.png)
Answer to Problem 12.26P
The mechanism for the given reaction is
Explanation of Solution
Diazomethane dissociates heterolytically when irradiated with ultraviolet light to produce a carbene and a nitrogen molecule.
The carbene then simultaneously adds to the initially double-bonded carbons. The lone pair on the carbene forms a bond with one carbon while the
The starting alkene has a trans geometry, therefore, the two substituents on the cyclopropane ring in the product are on opposite sides of the ring.
This means the product is chiral, and a racemic mixture of two enantiomers will be produced.
Thus, the complete mechanism for the reaction can be drawn as
A carbene adds to an alkene or alkyne to produce a cyclopropane ring.
(e)
Interpretation:
The mechanism for the reaction that will take place when the given compound is treated with
Concept introduction:
Diazomethane,
The stereochemistry of the double bond is preserved in the addition. If the double bond has a cis relationship, then the two substituents end up on the same side of the cyclopropane ring. If the two substituents on the double bond are trans to each other, they end up on the opposite sides of the cyclopropane ring. This also determines the product distribution if the cyclic product is chiral. If the starting alkene is achiral and the product chiral, the product is a racemic mixture of enantiomers. If the starting alkene is also chiral, then an unequal mixture of enantiomers is produced.
![Check Mark](/static/check-mark.png)
Answer to Problem 12.26P
The mechanism for the given reaction is
Explanation of Solution
Diazomethane dissociates heterolytically when irradiated with ultraviolet light to produce a carbene and a nitrogen molecule.
The carbene then simultaneously adds to the initially double-bonded carbons. The lone pair on the carbene forms a bond with one carbon while the
The starting alkene has a cis geometry and is symmetric. Therefore, only one product, a meso compound is produced.
Thus the complete mechanism for this reaction can be drawn as
A carbene adds to an alkene or alkyne to produce a cyclopropane ring.
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Chapter 12 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
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- You are tasked with creating a calibration curve for the absorbance of cobalt solutions of various concentrations. You must prepare 5 standards with concentrations between 1.00 mg/L and 10.0 mg/L Co2+. You have a stock solution with a concentration of 40 mg/L Co2+ and all the standard lab glassware including transfer pipets and flasks. Explain how you would make your 5 standard solutions of various concentrations, including what glassware you would use to measure and prepare each solution.arrow_forwardPredict the product and write the mechanism. CH3-CH=CH-CH2-CH3 + NBS- hv CCl4arrow_forwardHow exactly is carbon disulfide used in industry? Specifically, where does it come in during rubber or textile production and what is the chemical processes?arrow_forward
- A researcher has developed a new analytical method to determine the percent by mass iron in solids. To test the new method, the researcher purchases a standard reference material sample that is 2.85% iron by mass. Analysis of the iron standard with the new method returns values of 2.75%, 2.89%, 2.77%, 2.81%, and 2.87%. Does the new method produce a result that is significantly different from the standard value at the 95% confidence level?arrow_forwardCreate a drawing of an aceral with at least 2 isopropoxy groups, and a total of 11 carbon atomsarrow_forward4. Predict the major product(s) for each of the following reactions. HBr (1 equiv.) peroxide, A a. b. NBS, peroxide, Aarrow_forward
- In addition to the separation techniques used in this lab (magnetism, evaporation, and filtering), there are other commonly used separation techniques. Some of these techniques are:Distillation – this process is used to separate components that have significantly different boiling points. The solution is heated and the lower boiling point substance is vaporized first. The vapor can be collected and condensed and the component recovered as a pure liquid. If the temperature of the mixture is then raised, the next higher boiling component will come off and be collected. Eventually only non-volatile components will be left in the original solution.Centrifugation – a centrifuge will separate mixtures based on their mass. The mixture is placed in a centrifuge tube which is then spun at a high speed. Heavier components will settle at the bottom of the tube while lighter components will be at the top. This is the technique used to separate red blood cells from blood plasma.Sieving – this is…arrow_forwardBriefly describe a eutectic system.arrow_forward13.53 Draw all stereoisomers formed when each compound is treated with HBr in the presence of peroxides. a. b. C.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningEBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
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