
Concept explainers
(a)
Interpretation:
The product for the given nucleophilic elimination step with appropriate curved arrows is to be drawn.
Concept introduction:
In nucleophilic elimination step, the more electronegative atom bears full negative charge or partial negative charge. This is the electron rich atom, and the less electronegative atom bonded to the electronegative atom is relatively electron poor. The curved arrow drawn from the lone pair of electron rich atom points to bonding region between the more electronegative atom and less electronegative atom, representing the electron flow from the electron rich site to the electron poor site. The second curved arrow is drawn to represent the breaking of bond between the less electronegative atom and leaving group to avoid exceeding an octet on the less electronegative atom.
(b)
Interpretation:
The product for the given nucleophilic elimination step with appropriate curved arrows is to be drawn.
Concept introduction:
In nucleophilic elimination step, the more electronegative atom bears full negative charge or partial negative charge. This is the electron rich atom, and the less electronegative atom bonded to the electronegative atom is relatively electron poor. The curved arrow drawn from the lone pair of electron rich atom points to bonding region between the more electronegative atom and less electronegative atom, representing the electron flow from the electron rich site to the electron poor site. The second curved arrow is drawn to represent the breaking of bond between the less electronegative atom and leaving group to avoid exceeding an octet on the less electronegative atom.

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Chapter 7 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
- Assign this spectrumarrow_forwardRedraw the tripeptide with or without its acidic hydrogensto demonstrate where the total charge of -2 comes from: *see imagearrow_forward2. Consider the data below to answer the following questions. Cyanohydrins are important intermediates in the synthesis of α-hydroxycarboxylic acids from ketones and aldehydes. The nitrile functional group can be hydrolyzed by aqueous acid to yield a carboxylic acid. Nitriles can also be hydrolyzed to carboxylic acids using aqueous base. Unfortunately, when a cyanohydrin is treated with aqueous base the original carbonyl compound is isolated. OH CH-COOH 0 HO CN C H30* C. H H HC N NaOH H₂O C=O 0 cyanohydrin H + NaCN + H₂Oarrow_forward
- Assign all integrated peaksarrow_forward- Consider the data in the Table below to answer the following questions: Acidities of Substituted Benzoic and Acetic Acids pk,s at 25C Y-CH COOH Y Y - CH₂COOH meta para H 4.75 4.19 4.19 2.47 3.64 3.55 3.57 4.09 4.46 CN OCH 3 A. Draw the structure of the strongest acid in the table above. B. Explain why cyanoacetic acid and methoxyacetic acid are more acidic than their correspondingly substituted benzoic acid counterparts.arrow_forwardDraw the curved arrow mechanism for this reaction starting with 2-propanol in sulfuric acid. Show all nonzero formal charges and all nonbonded electrons in each step. Species not involved in a particular step do not need to be included in that step, and resonance forms do not need to be shown. Note that the alcohol is in much higher concentration than H₂O in this reaction. Harrow_forward
- Provide reactions showing the following conversions: * see imagearrow_forward. Draw structures corresponding to each of the following names or Provide IUPAC names for each of the ollowing structures [for 4 ONLY]. A. 2-propylpentanoic acid. B. m-chlorobenzoic acid. D. C. O O HOC(CH2)3COH glutaricadd OH OH H3C CH3 C=C H COOH salicylicadd tiglicadd CH₂C=N Joe Marrow_forward. Provide structure(s) for the starting material(s), reagent(s) or the major organic product(s) of each of the ollowing reactions or sequences of reactions. Show all relevant stereochemistry [five only] A. O B. OET CH3 1. LIAIH, ether 2 H₂O O (CH3)2CH-C-CI + 0 0 ether (CH3)2CH-C-O-C-CH3 CH3 C. 0 OH HO CH3 ° Clarrow_forward
- How would you prepare each of the following compounds using either an acetoacetic ester synthesis or a alonic ester synthesis? Show all intermediate structures and all reagents.[Three only] A. B. COOH OH C. D. 0 H2C CHCH2CH2CCH3arrow_forwardFats and greases have mostly aliphatic regions which are hydrophobic. Provide a schematic of howsoaps/detergents remove fats and grease from the soiled material. * see imagearrow_forwardWhat chemical has the common name "lye"? Pick one of the 3 esters and show the hydrolysis mechanism to make a carboxylic acid. The organic “R” should be used to limit the redrawing time of the entire molecule. * see imagearrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
