(a)
Interpretation:
The nucleophile that reacts faster with
Concept introduction:
The nucleophilic substitution reaction
Nucleophiles are the electron-rich species that donate the electron pair to the electron-deficient species in the reaction. The electron-deficient species are known as the electrophiles.
(b)
Interpretation:
The substrate that reacts faster with
Concept introduction:
The nucleophilic substitution reaction
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General Chemistry: Principles and Modern Applications (11th Edition)
- Which of the following synthetic sequences would not accomplish the transformation shown? (A) (B) (C) (D) O A O B O C O TSCI pyridine PBr3 OH SOCI₂ pyridine NaCECH Mgº Et₂O 1) DMSO, (COCI)2 2) NEt3 BrMg 1) NaCECH H-B at 1) 2) H₂O₂, NaOH 1) 2) H₂O O H 2) H₂O 1) TSCI pyridine 2) IBUOK H₂ Lindlar's cat. 1) TSCI pyridine 2) IBUOK H 1) BH3-THF 2) H₂O₂, NaOH 1) 03 2) Me₂S 1) H₂, Pt 2) H3O+ PCC Dess-Martin Periodinane CH₂Cl₂arrow_forwardRank the nucleophiles in following group in order of increasing nucleophilicity. −OH, −NH2, H2Oarrow_forwardOCH3 NO₂ A A OCH3 NHCCH3 B Reaction: Nitration Which compound (A, B, or C) reacts the fastest? Which compound (A, B, or C) reacts the slowest? F B NO₂ Reaction: Bromination C C Which compound (A, B, or C) reacts the fastest? Which compound (A, B, or C) reacts the slowest? + + +arrow_forward
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- Pleas explain how this process occurs. Identify SN1, SN2, E2, E1, nucleophiles and electrophiles.arrow_forwardDraw a plausible mechanism for the following reactions, showing relevant lone pairs and arrow pushing. Do not consider stereochemistry in your mechanism. a) H,SO4, EtOH b) OH H,SO, Heatarrow_forwardWhat is the correct sequence of steps for the following transformation? Step 1 Step 2 HO (a) HBr, followed by H20 (b) H2 over Lindlar's catalyst, followed by H2O/H,SO4 (c) H2O/H2SO4/H&SO4, followed by HBr (d) H2 over Pd/C, followed by H20 Which structure corresponds to the missing step in the reaction mechanism for the conversion of the alkene/alcohol to the cyclic ether? HC! H20 + H;O OH OH OH (a) (b) (c) (d)arrow_forward
- Which of the following statements about nucleophilic reactions are generally true ? V SN2 reactions rely on least hindered substrates. 1° are best while 3° are worst. V SN1 and E1 reactions rely on good carbocation forming substrates. Benzylic, allylic, 3° are best while 1° are worst. V E2 reactions depend primarily on strong bases like hydroxides, alkoxides, or amides. V Polar aprotic solvents like HMPA, DMF, DMSO, acetonitrile, or acetone are favoring SN2. V Polar protic, neutral or acidic solvents/environments like alcohols, water, or acidic solutions favor SN1/E1 mechanisms. SN2 and E2 reactions are stereospecific, while SN1 occurs with racemization. Elimination reactions are expected to result in Zaitsev's (more substituted) product(s), unless hinderance steers them into Hoffman's (less substituted) product(s).arrow_forwardWhat is the major elimination product obtained from the following reaction? CH3 CH3 NaOCH₂CH3 HOCH₂CH3 Ot-Bu || CH3 Ot-Bu ||| CH3 IV CH3arrow_forwardH3C-C ethanal :O: H + H-C=N hydrogen cyanide CN OH H3C-C-C=N: H ethanal cyanohydrin In this reaction, cyanide ion is consumed in step 1 and regenerated in step 2. The reaction does not proceed in the absence of cyanide. Besides acting as a nucleophile, the role of cyanide is that of aarrow_forward
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