(a)
Interpretation:
The mechanism for the given reaction has to be proposed.
Concept introduction:
Carboxylic acid shows nucleophilic acyl substitution reaction. The acid protonates the oxygen of carboxylic acid which results in increased electrophilicity of the carbonyl carbon. The water molecule acts as a nucleophile and gets attached to the carbonyl carbon of the carboxylic acid. The tetrahedral intermediate is formed stays in equilibrium with protonated and unprotonated form. The
(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 (3rd Edition)
- The Baylis–Hillman reaction is a DABCO (1,4-diazabicyclo[2.2.2]octane) catalyzed reaction of an a,b-unsaturated carbonyl compound with an aldehyde to form an allylic alcohol. Propose a mechanism for the reaction. (Hint: DABCO serves as both a nucleophile and as a base in the reaction.)arrow_forward1. Starting from the compound on the left, synthesize the target product on the right using any readily available reagents. The product can be made by 7 steps or less, but any synthesis route that correctly leads to the product will be accepted. 2. Starting from the compound on the left, synthesize the target product on the right using any available reagents.arrow_forwardIn the box to the left of each reaction below, write the mechanism by which it occurs (could be SN1, SN2, or E1, or even 2 of them). Then draw the product(s).arrow_forward
- A carboxylic acid is formed when an a-haloketone reacts with hydroxide ion. This reaction is called a Favorskii reaction. Propose a mechanism for thefollowing Favorskii reaction. (Hint: In the first step, HO- removes a proton from the a-carbon that is not bonded to Br; a three-membered ring is formedin the second step; and HO- is a nucleophile in the third step.)arrow_forward1. Which of the following is the strongest nucleophile? Refer to the diagram below with an MeOH, MeSH, etc. 2. Which of the following is true about the stereochemistry of SN1 reaction?a.retention of configuration at the electrophilic centerb.50:50 mixture of retention and inversion of configuration at the electrophilic centerc.inversion of configuration at the electrophilic centerd. slightly more inversion than retention at the electrophilic centerarrow_forward1. What type of reaction is occuring in step 3? (halogenation, hydrohalogenation, reduction, keto–enol tautomerism, dehydrohalogenation, acid-catalyzed hydration, base-catalyzed hydration) 2. Which reagent is necessary for step 3? (Br2, HBr, H2/Pt, NaNH2, H20/H2SO4/HgSO4)arrow_forward
- Draw the molecule: Under second-order conditions (strong base/nucleophile), SN2 and E2 reactions may occur simultaneously and compete with each other.Show what products might be expected from the reaction of 2-bromo-3-methylbutane (a moderately hindered 2∘∘ alkyl halide) with sodium ethoxide. Do not worry about sterechemistry inther SN2 product for this problem. Don't forget about stereochemistry.arrow_forwardPlease help me to select the correct reagents for the following 3 steps.arrow_forwardMap out a multi-step synthesis for the transformation below, indicating specific reagents/products for each step.arrow_forward
- Chemistry Find the most efficient synthetic route for the followinf transformations.arrow_forwardA carboxylic acid is formed when an a-haloketone reacts with hydroxide ion. This reaction is called a Favorskii reaction. Propose a mechanism for the following Favorskii reaction. (Hint: In the first step, HO- removes a proton from the a-carbon that is not bonded to Br; a three-membered ring is formed in the second step; and HO- is a nucleophile in the third step.)arrow_forwardWhich of A to E shows the structure of the major product obtained from the E1 reaction shown below?arrow_forward
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning