Consider this reaction: Br CH;OH Br-Br H3CO The mechanism proceeds through a first cationic intermediate, intermediate 1. Nucleophilic attack leads to intermediate 2, which goes on to form the final product. In cases that involve a negatively charged nucleophile, the attack of the nucleophile leads directly to the product. Br + CH3OH Br Intermediate 1 Intermediate 2 (product) In a similar fashion, draw intermediate 1 and intermediate 2 (final product) for the following reaction. OH + Br2 + HBr Br racemic mixture

Consider this reaction: Br CH;OH Br-Br H3CO The mechanism proceeds through a first cationic intermediate, intermediate 1. Nucleophilic attack leads to intermediate 2, which goes on to form the final product. In cases that involve a negatively charged nucleophile, the attack of the nucleophile leads directly to the product. Br + CH3OH Br Intermediate 1 Intermediate 2 (product) In a similar fashion, draw intermediate 1 and intermediate 2 (final product) for the following reaction. OH + Br2 + HBr Br racemic mixture

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter19: Enolate Anions And Enamines

Section19.9: Crossed Enolate Reactions Using Lda

Problem JQ

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Consider this reaction: Br CH;OH Br-Br H3CO The mechanism proceeds through a first cationic intermediate, intermediate 1. Nucleophilic attack leads to intermediate 2, which goes on to form the final product. In cases that involve a negatively charged nucleophile, the attack of the nucleophile leads directly to the product. Br + CH3OH Br Intermediate 1 Intermediate 2 (product) In a similar fashion, draw intermediate 1 and intermediate 2 (final product) for the following reaction. OH + Br2 + HBr Br racemic mixture
1c. What is the nucleophile in the following reaction? .Br CH;CO0 Na LO OCCH3 NaBr ld. What is the electrophile in the following reaction? Br CH;COO Na L0OCCH3 NaBr +
4. A CHEM 245 student wants to synthesize some ethylene glycol to use as antifreeze in his radiator this winter. He proposes the following reaction to his instructor, who quickly explains that this reaction won't work as proposed due to the student's choice of reagent. 1) NaH 2) H20 OH Но a) Why can't sodium hydride (NaH) be used as the nucleophile in the reaction above? b) Propose an alternate reagent that COULD be used with the ethylene oxide to successfully give the desired ethylene glycol product.
6. Complete the following reaction scheme (g) CH H3C. 1) 9-BBN CH 2) H-О, NaOH (h) H20, H,SO4. HØSO4 (i) 1) BH3 2) H2O,, NaOH
The mechanism proceeds through a first cationic intermediate, intermediate 1. Nucleophilic attack leads to intermediate 2, which goes on to form the final product. In cases that involve negatively charged nucleophile, the attack of the nucleophile leads directly to the product. H. Br + CH3OH Br Intermediate 2 (product) Intermediate 1 In a similar fashion, draw intermediate 1 and intermediate 2 (final product) for the following reaction. OCH3 Cl2 MEOH ĆI racemic mixture Pay attention to the reactants, they may differ from the examples. In some reactions, one part of the molecule acts as the nucleophile. • You do not have to consider stereochemistry. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate intermediate 1 and intermediate 2 using the the dropdown menu. → symbol from
What Is the starting materlal of this reaction? Click on a letter A through D to answer. CH,OH H+ cat. А. С. В. OH D.
1) For each reaction below, provide the product and type (ketone/aldehyde/enol/enolate) of the reactant and the product. The equilibrium arrows are generic: a) Туре b) Туре c) Type d) Type OH ]}₁ OH H3O* catalyst H₂O H3O* catalyst H₂O OH catalyst H₂O OH catalyst H₂O Product Туре Product Type Product Type Product Type
1) For each reaction below, provide the product and type (ketone/aldehyde/enol/enolate) of the reactant and the product. The equilibrium arrows are generic: a) Type b) Type c) Type d) Type OH 0}₁ OH H3O* catalyst H₂O H3O* catalyst H₂O OH catalyst H₂O OH catalyst H₂O Product Type Product Type Product Type Product Type
Place the intermediates in the correct order to complete the mechanism for the following reaction. Reaction: HO H. но, HO H. OH HO. H.
Predict the products of this organic reaction: CH3 CH₂ || No reaction CH3 -CH-CH₂-CH3 + NaOH A Specifically, in the drawing area below draw the 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. ? Click anywhere to draw the first atom of your structure. X Ś
LOH NaOH `N' (S) H20 'N' ČI This nucleophilic substitution occurs with rearrangement. Draw curved arrows to show the movement of electrons in the following step of the reaction mechanism. Arrow-pushing Instructions OH :OH N. H.
Complete the following reaction sequence with the missing major organic products. CH, NaOH CH,CH,CH,CHCH,CHCH,CEN H20 NaOH H,0 CH,CH,