Classify the following substituents according to whether they are electron donors or electron acceptors relative to hydrogen by the resonance and the inductive mechanisms. a = acceptor d = donor n = no effect :O: 1. Inductive effect Resonance effect -CH=CH-C-CH3 2. -NHCH,CH,CH,C=N: Inductive effect Resonance effect :o: 3. Inductive effect| Resonance effect -CH,CH,CH,CH,OH

Classify the following substituents according to whether they are electron donors or electron acceptors relative to hydrogen by the resonance and the inductive mechanisms. a = acceptor d = donor n = no effect :O: 1. Inductive effect Resonance effect -CH=CH-C-CH3 2. -NHCH,CH,CH,C=N: Inductive effect Resonance effect :o: 3. Inductive effect| Resonance effect -CH,CH,CH,CH,OH

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy

Section13.SE: Something Extra

Problem 56GP: Long-range coupling between protons more than two carbon atoms apart is sometimes observed when ...

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Long-range coupling between protons more than two carbon atoms apart is sometimes observed when bonds intervene. An example is found in 1-methoxy-l-buten-3-yne. Not only does the acetylenic proton, Î—a, couple with the vinylic proton Hb, it also couples with the vinylic proton Hc, four carbon atoms away. The data are: Construct tree diagrams that account for the observed splitting patterns of Î—a, Hb, and Hc.
Cyclohex-2-enone has two protons on its carbon–carbon double bond (labeled Ha and Hb) and two protons on the carbon adjacent to the double bond (labeled Hc). (a) If Jab = 11 Hz and Jbc = 4 Hz, sketch the splitting pattern observed for each proton on the sp2 hybridized carbons. (b) Despite the fact that Ha is located adjacent to an electron-withdrawing C = O, its absorption occurs upeld from the signal due to Hb (6.0 vs. 7.0 ppm). Offer an explanation.
Cyclohex-2-enone has two protons on its carbon-carbon double bond (labeled Ha and Hb) and two protons on the carbon adjacent to the double bond (labeled Hc). (a) If Jab = 11 Hz and Jbc = 4 Hz, sketch the splitting pattern observed for each proton on the sp2 hybridized carbons. (b) Despite the fact that Ha is located adjacent to an electron-withdrawing C=O, its absorption occurs upfield from the signal due to Hb (6.0 vs. 7.0 ppm). Offer an explanation.
Cyclohex-2-enone has two protons on its carbon–carbon double bond (labeled Ha and Hb) and two protons on the carbon adjacent to the double bond (labeled Hc). (a) If Jab = 11 Hz and Jbc = 4 Hz, sketch the splitting pattern observed for each proton on the sp2 hybridized carbons. (b) Despite the fact that Ha is located adjacent to an electron-withdrawing C = O, its absorption occurs upfield from the signal due to Hb (6.0 vs. 7.0 ppm). Offer an explanation.
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3. Which one of the following structures represents major resonance contributor of the molecule in the box? A) CH,-CEN-c B) CH,-č=N=Ö: CH,-C=N=ö: C) CH,-CEN=ö: D) CH,-C=N-0: OB Oc O A OD Question 4 4. Which one of the following structures represents the resonance contributor of a molecule in the box in agreement with the shown curved arrows? A) H,C-NEN: B) H,C-NEN: H,C=N=N: C) H,C=NEN: D) H,C-N=N: OC OB OA OD
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