Concept explainers
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(a)
Interpretation:
How the given compound with specified stereochemistry can be produced from an
Concept introduction:
A cyclopropyl group can be introduced in a compound by reacting the corresponding alkene (or
The stereochemistry of the double bond is preserved in the reaction as it is a concerted addition. If the alkene has a cis configuration, the two similar substituents on the double bond end up on the same side of the cyclopropyl ring in the product. If it is a trans alkene, the similar substituents on the double bond end up on opposite sides of the ring in the product.
Carbenes are generated in situ, typically by irradiating a mixture of the alkene and diazomethane with UV light or by treating a mixture of the alkene and haloform (trihalomethane) with a strong base like an alkoxide.
(b)
Interpretation:
How the given compound with specified stereochemistry can be produced from an alkene is to be shown along with the reagents used and special conditions if any.
Concept introduction:
A cyclopropyl group can be introduced in a compound by reacting the corresponding alkene (or alkyne) with a carbene. A carbene is a species with only two groups, typically hydrogen or halogen atoms bonded to a carbon. The carbon atom also carries a lone pair of electrons or sometimes two unpaired electrons. This pair of electrons makes the carbene extremely reactive. Carbenes add to an alkene or alkyne by simultaneously forming bonds with the two carbon atoms from the double (or triple) bond. One bond is formed by the lone pair on the carbene and the other by the
The stereochemistry of the double bond is preserved in the reaction as it is a concerted addition. If the alkene has a cis configuration, the two similar substituents on the double bond end up on the same side of the cyclopropyl ring in the product. If it is a trans alkene, the similar substituents on the double bond end up on opposite sides of the ring in the product.
Carbenes are generated in situ, typically by irradiating a mixture of the alkene and diazomethane with UV light or by treating a mixture of the alkene and haloform (trihalomethane) with a strong base like an alkoxide.
(c)
Interpretation:
How the given compound with specified stereochemistry can be produced from an alkene is to be shown along with the reagents used and special conditions if any.
Concept introduction:
A cyclopropyl group can be introduced in a compound by reacting the corresponding alkene (or alkyne) with a carbene. A carbene is a species with only two groups, typically hydrogen or halogen atoms bonded to a carbon. The carbon atom also carries a lone pair of electrons or sometimes two unpaired electrons. This pair of electrons makes the carbene extremely reactive. Carbenes add to an alkene or alkyne by simultaneously forming bonds with the two carbon atoms from the double (or triple) bond. One bond is formed by the lone pair on the carbene and the other by the
The stereochemistry of the double bond is preserved in the reaction as it is a concerted addition. If the alkene has a cis configuration, the two similar substituents on the double bond end up on the same side of the cyclopropyl ring in the product. If it is a trans alkene, the similar substituents on the double bond end up on opposite sides of the ring in the product.
Carbenes are generated in situ, typically by irradiating a mixture of the alkene and diazomethane with UV light or by treating a mixture of the alkene and haloform (trihalomethane) with a strong base like an alkoxide.
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Chapter 12 Solutions
Organic Chemistry: Principles And Mechanisms (second Edition)
- Predict the products of this organic reaction: O CH3 + H2O + HCI A A? CH3-CH2-C-N-CH3 Specifically, in the drawing area below draw the condensed structure of the product, or products, of this reaction. If there's more than one product, draw them in any arrangement you like, so long as they aren't touching. If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area. No Reaction Click anywhere to draw the first atom of your structure.arrow_forwardWhat is the missing reactant in this organic reaction? R+ HO-C-CH2-CH3 0= CH3 CH3 —CH, C−NH—CH CH3 + H₂O Specifically, in the drawing area below draw the condensed structure of R. If there is more than one reasonable answer, you can draw any one of them. If there is no reasonable answer, check the No answer box under the drawing area. Note for advanced students: you may assume no products other than those shown above are formed. No Answer Click anywhere to draw the first atom of your structure. €arrow_forward个 CHEM&131 9267 - $25 - Intro to Mail - Hutchison, Allison (Student x Aktiv Learnin https://app.aktiv.com Draw the product of the reaction shown below. Ignore inorganic byproducts. + Na2Cr2O7 Acetone, H2SO4 Type here to search Dryng OH W Prarrow_forward
- Predict the products of this organic reaction: OH + NaOH A? Specifically, in the drawing area below draw the skeletal ("line") structure of the product, or products, of this reaction. (If there's more than one product, draw them in any arrangement you like, so long as they aren't touching.) If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area. No reaction Click and drag to start drawing a structure. ✓ Sarrow_forwardPredict the products of this organic reaction: CH3-C-O-CH2-CH2-C-CH3 + H₂O ? A Specifically, in the drawing area below draw the condensed structure of the product, or products, of this reaction. (If there's more than one product, draw them in any arrangement you like, so long as they aren't touching.) If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area. No reaction Click anywhere to draw the first atom of your structure. :☐ darrow_forwardDE d. Draw an arrow pushing mechanism for the following IN O CI N fo 人 P Polle DELL prt sc home end ins F5 F6 F7 F8 F9 F10 F11 F12arrow_forward
- Predict the products of this organic reaction: + H₂O H* ? A Specifically, in the drawing area below draw the skeletal ("line") structure of the product, or products, of this reaction. (If there's more than one product, draw them in any arrangement you like, so long as they aren't touching.) If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area. No Reaction Click and drag to start drawing a structure.arrow_forwardPredict the major organic products of the reaction below and draw them on right side of the arrow. If there will be no significant reaction, check the box below the drawing area instead. C Cl CH, OH There will be no significant reaction. + pyridine G Click and drag to start drawing a structure.arrow_forwardWhat is the missing reactant in this organic reaction? H R+ H2O Δ OH 0= CH3-CH-O-CH3 + CH3-C-OH Specifically, in the drawing area below draw the condensed structure of R. If there is more than one reasonable answer, you can draw any one of them. If there is no reasonable answer, check the No answer box under the drawing area. No Answer Click anywhere to draw the first atom of your structure. dyarrow_forward
- You are trying to determine whether the following organic reaction can be done in a single synthesis step. If so, add any missing reagents or conditions in the drawing area below. If it isn't possible to do this reaction in a single synthesis step, check the box below the drawing area instead. Note for advanced students: if you have a choice of reagents to add, you should choose the least reactive and most economical reagents possible. Cl It isn't possible to do this reaction in a single synthesis step. + T OHarrow_forwardPredict the products of this organic reaction: CH3 O CH3-CH-C-O-CH2-CH2-CH3 + H₂OH+ Η ? A Specifically, in the drawing area below draw the condensed structure of the product, or products, of this reaction. (If there's more than one product, draw them in any arrangement you like, so long as they aren't touching.) If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area. No Reaction Click anywhere to draw the first atom of your structure.arrow_forward€ CH3-CH-C-O-CH2-CH2-CH3 + NaOH A? Specifically, in the drawing area below draw the condensed structure of the product, or products, of this reaction. (If there's more than one product, draw them in any arrangement you like, so long as they aren't touching.) If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area. Predict the products of this organic reaction: CH3 O Click anywhere to draw the first atom of your structure. No reaction ✓ Garrow_forward
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning