Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 25.8, Problem 21P
The fluoro-substitued geranyl pyrophosphate shown here reacts with isopentenyl pyrophosphate to form fluoro-substitued farnesyl pyrophosphate. The
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When n-butyl bromide is treated with sodium iodide (Nal) in ethanol (EtOH), the concentration of iodide quickly decreases, but then
slowly returns to its original concentration. Provide an explanation for these observations, and identify the final product of the
reaction.
Olodide displaces the bromide leaving group, and then bromide displaces the iodide leaving group.
Olodide displaces the bromide leaving group, and the resulting n-butyl iodide undergoes an E2 elimination.
Olodide displaces the bromide leaving group, and the resulting n-butyl iodide undergoes an E2 elimination.
O lodide displaces the bromide leaving group, and the resulting n-butyl iodide undergoes a substitution with EtOH.
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In a Wittig reaction, a ketone or aldehyde reacts as an electrophile with a nucleophile called a Wittig reagent (or phosphonium ylide) to produce an alkene. The Wittig reagent is commonly synthesized first in a two-step process beginning with an alkyl halide, then reacted with the carbonyl compound. In this problem, you'll explore the mechanism of a multi-step synthesis to make an alkene using the Wittig approach.
When acetone is dissolved in either a slightly
basic or a slightly acidic solution of oxygen-18
labeled water, H2180, oxygen-18 labeled acetone,
(CH3)2C=180, is produced. This is a form of an
isotopic exchange reaction between acetone and water. Provide a mechanism to account for this reaction in (a) basic
solution and (b) acidic solution. Hint: Is the addition of the nucleophile reversible or irreversible?
180
+ H,180
CH3
+ Hо
`CH3
Acid or base
H3C
H3C
Chapter 25 Solutions
Organic Chemistry (8th Edition)
Ch. 25.1 - Prob. 1PCh. 25.3 - Which has a higher melting point, glyceryl...Ch. 25.3 - Draw the structure of an optically inactive fat...Ch. 25.3 - Draw the structure of an optically active fat...Ch. 25.5 - Do the identities of R1 and R2 in phosphatidic...Ch. 25.5 - Membranes contain proteins, Integral membrane...Ch. 25.5 - Prob. 8PCh. 25.5 - The membrane phospholipids in deer have a higher...Ch. 25.6 - Treating PGC2 with a strong base such as sodium...Ch. 25.7 - Mark off the isoprene units in menthol, -selinene,...
Ch. 25.7 - Prob. 13PCh. 25.7 - Prob. 14PCh. 25.8 - Propose mechanisms for the Claisen condensation...Ch. 25.8 - Prob. 16PCh. 25.8 - Propose a mechanism for the conversion of...Ch. 25.8 - Propose a mechanism for the biosynthesis of...Ch. 25.8 - Propose a mechanism for the conversion of the E...Ch. 25.8 - The fluoro-substitued geranyl pyrophosphate shown...Ch. 25.8 - Prob. 22PCh. 25.8 - Prob. 23PCh. 25.9 - Draw the individual 1,2-hydride and 1,2-methyl...Ch. 25.10 - Prob. 26PCh. 25.10 - Prob. 27PCh. 25.10 - The acid component of a cholesterol ester is a...Ch. 25.10 - Prob. 29PCh. 25.10 - Prob. 30PCh. 25 - Prob. 31PCh. 25 - An optically active fat, when completely...Ch. 25 - Prob. 33PCh. 25 - a. How many different triacylglycerols are there...Ch. 25 - Cardiolipins are found in heart muscles. Draw the...Ch. 25 - Nutmeg contains a simple, fully saturated...Ch. 25 - Draw the product that is obtained from the...Ch. 25 - Prob. 39PCh. 25 - Prob. 40PCh. 25 - Propose a mechanism for the biosynthesis of...Ch. 25 - 5-Androstene-3.17-dione is isomerized to...Ch. 25 - Prob. 44PCh. 25 - Eudesmol is a sesquiterpene found in eucalyptus....Ch. 25 - Prob. 46PCh. 25 - Prob. 47PCh. 25 - Diethylstilbestrol (DES) was given to pregnant...
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- Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. You do not have to consider stereochemistry. Include all valence lone pairs in your answer. Do not include counter-ions, e.g., Na+, I-, in your answer. In cases where there is more than one answer, just draw one.arrow_forwardAcyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. You do not have to consider stereochemistry. Include all valence lone pairs in your answer. Do not include counter-ions, e.g., Na+, I-, in your answer. In cases where there is more than one answer, just draw one.arrow_forwardThe acetoacetic ester synthesis is a carbonyl alkylation reaction. It is used to prepare methyl ketones from primary alkyl halides, lengthening the carbon chain by three atoms. Thus, the product can be visualized as being a "substituted acetone." The reaction consists of three steps: generation of the enolate anion followed by SN2 reaction with a primary alkyl halide, ester hydrolysis under acid conditions, and decarboxylation. м Br H3C H3C OEt 1. NaOEt 2. H₂O* 3. heat H₂C. Draw curved arrows to show the movement of electrons in this step of the mechanism. CO₂ EtOH CH3 Arrow-pushing Instructions H3C 1:0: :0: :Br: Br: H₂C CH3 CH3 H3C CH3 7barrow_forward
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