(a)
Interpretation:
The mechanism for the given reaction has to be proposed.
Concept introduction:
(b)
Interpretation:
To predict the reside of labeled oxygen in the product when a carboxylic acid is dissolved in isotopically labeled methanol and acid catalyst is added to it.
Concept introduction:
Carboxylic acid reacts with alcohol in the presence of a strong acid to form an ester. Carbonyl oxygen of carboxylic acid gets protonated by the acid resulting in increased electrophilicity of the carbonyl carbon. Alcohol can act as a nucleophile which gets attached to the carbonyl carbon after that tetrahedral intermediate is formed. A proton is removed from alkoxy group (
(c)
Interpretation:
To predict the labeled reside in the product when ester is dissolved in isotopically labeled water(
Concept introduction:
Ester undergoes hydrolysis when dissolved in water with acid. Carbonyl oxygen of ester gets protonated by the acid resulting in increased electrophilicity of the carbonyl carbon. Water can act as a nucleophile which gets attached to the carbonyl carbon of ester after that tetrahedral intermediate is formed. A proton is removed from
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Chapter 11 Solutions
Essential Organic Chemistry, Global Edition
- Fill in the boxes with reagents or products and show the mechanism.arrow_forwardAn unsaturated ketone is converted to the 3-cyano derivative shown below. Which reagent could be used to accomplish this? CEN O 1. HCN (hydrogen cyanide) O 2. Methylmagnesium bromide followed by ammonia. O 3. Dimethylcopper lithium followed by sodium amide. O 4. Methylamine followed by a dehydrating agent like P205-arrow_forward14. Adding NaCN to the carbonyl compound poses the risk of making HCN, which is poisonous. How can this risk be mitigated? Add NaOH first, then NaCN Add NaCN first, then NaOH Add NaHSO3 first, then NaCN Add NaOH first, then NaHSO3 NOTE: ONLY ANSWER NUMBER 14arrow_forward
- Predict the heterocyclic product E from the reaction below and give a curly arrow mechanism. Ph. O Et NHẠC i G base, POCI Give the structure of the heterocyclic product H and show the reaction intermediate G after step 1. Give a mechanism for step 1 step 2. 1. POCIĄ 1. BuLi 2. CO₂ 3. H*, H₂O 2 ENH E Give the structure of the heterocyclic product G and show the reaction intermediates after both steps 1 and 2. G Harrow_forwardBr CH3OH + 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 • 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 → symbol from the dropdown menu.arrow_forwardPropose a mechanism for the attached reaction. Please type or use ChemDraw (not write) so that solution is clear.arrow_forward
- 10:54 ← Question 21 of 32 Draw the major product of this reaction. Ignore inorganic byproducts. Submit Assume that the water side product is continuously removed to drive the reaction toward products. (CH3)2NH, TSOH Select to Draw | I Iarrow_forward2. Draw a detailed mechanism for the following reactions. You do not need to draw arrow steps for the hydrogenation reaction. Ph 1. NaOH 2. CH31 3. H₂ Pd/C 4. H30* HBr en Ph^ Brarrow_forward1. Provide the MECHANISM for the following reaction. Do not add any new reagents. O + H3C O =CH ₂ NaOEt EtOHarrow_forward
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
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