Interpretation:
A pair of nucleophiles is to be found from Tables 9-1 and 9-10 whose relative nucleophilicities in ethanol are the reverse of what they are in DMF. Also, what this observation suggests as to which of the two species is more strongly solvated in ethanol is to be given.
Concept introduction:
In a reaction, the species which gives an electron pair to create a
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Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
- Me MeOH Ме Me Ме Me Me -Br Br (RDS) H' Et \'H Et Et H Et A Br Me Ме + en HBr H' Et 1. Complete the mechanism above by filling in curved arrows to depict electron flow. Is the MeOH nucleophile involved in the RDS (rate determining step)?arrow_forwardFigure 9-4 D H Br Фон H DOM OHarrow_forward3) Any compound or ion with at least one lone pair can be considered a base and/or a nucleophile. The relative basicity and nucleophilicity of the species is one of the most important factors that determine the mechanism of a reaction on sp³-carbon atoms. Please show an example of a) a reagent that is a strong nucleophile and a strong base, b) a reagent that is a weak nucleophile and a strong base, c) a reagent that is a strong nucleophile and a weak base, d) a reagent that is a weak nucleophile and a weak base. Which nitrogen atom in the structure below is most nucleophilic? Please explain by discussing the electron density around each nitrogen atom. Show at least three resonance structures of the compound. N.arrow_forward
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- What is the energy diagram of the following Sn1 reaction. 2-chloro-2-methylpropane + H2O -> 2-methylpropan-2-ol + HCl write the rate law equationarrow_forwardFor the following reactions, design the experimental conditions that willlead to the suggested major products. Suggest actual reagents, solvents, nucleophile/base, concentration of nucleophile/base and what mechanism it is. Do not just use descriptors.arrow_forwardWhen HCI, HBr, and HI were used as HX in the next reaction, the rates of all reactions were almost the same. below Answer the question. OH HX CH3 CH3 H2O (1) Show the ions that act as each nucleophile in order from the one that is considered to have the highest nucleophilic reactivity. (2) Explain the reason why you thought that the order was (1). (3) Explain why the reaction rates were almost the same regardless of which HX was used. (4) Nax was used instead of HX, but the reaction did not proceed. Explain the reason for this.arrow_forward
- Choose the best option for the immediate nucleophile precursor to 2-methylbutane. A LiCu LiCu E BrMg 2 2 electrophile nucleophile B LiCu D (CH3CH2)2CuLi 2arrow_forwardwas reading the organic chemical literature and was surprised to read that this structure reacts with good Lewis/attacker nucleophiles rapidly by the SN1 pathway. Why was Prof. surprised by these data? Explain these data using your knowledge of SN1 pathways. Prof. Me xo Me Me OTSarrow_forwardOrganometallic reagents and alkoxides are strong bases as well as being good nucleophiles. Given the pKa values below, which reagent is the stronger base, nBuLi (CH3CH2CH2CH2LI) or the tert-butoxide anion ((CH3)3CO‒)? Explain your choice clearly in terms of structure andbonding. (Comparing the pKa values is not an explanation.) (CH3)3COH pka= 16.54CH3CH2CH2CH3 pka= 50arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningEBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT