Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 6.SE, Problem 47AP
The naturally occurring molecule α-terpineol is biosynthesized by a route that includes the following step:
(a) Propose a likely structure for the isomeric carbocation intermediate.
(b) Show the mechanism of each step in the biosynthetic pathway, using curved arrows to indicate electron flow.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
(a) What happens when CH3—O—CH<sub3 is heated with HI?(b) Explain mechanism for hydration of acid catalyzed ethene :CH2 = CH2 + HzO CH3—CH,—OH
Draw the product of the following Lewis acid-base reaction. Discuss whether the
product will retain its monomeric form or if it will dimerise and why.
(c)
Ph
Toluene
AICI
CHO
Ph
Compound X (C4H9Br) reacts by heating with NaOH in H2O to form Y. The
compound Y then undergoes acid catalysed hydration by H2SO4 in 180°C to
form 2-methyl prop-1-ene.
(e) Determine the structure of X and Y.
(f) Predict a MAJOR product when compound Y reacts with H2SO4 in
140°C.
(g) Draw a structural isomer of X. Name the isomer using IUPAC
nomenclature.
(h) Describe a chemical test to distinguish between compound Y and
1-butanol.
Chapter 6 Solutions
Organic Chemistry
Ch. 6.1 - Prob. 1PCh. 6.3 - Prob. 2PCh. 6.3 - Using curved fishhook arrows, propose a mechanism...Ch. 6.4 - Prob. 4PCh. 6.4 - An electrostatic potential map of boron...Ch. 6.5 - What product would you expect from reaction of...Ch. 6.5 - Reaction of HBr with 2-methylpropene yields...Ch. 6.6 - Prob. 8PCh. 6.6 - Predict the products of the following polar...Ch. 6.7 - Which reaction is more energetically favored, one...
Ch. 6.7 - Prob. 11PCh. 6.9 - Which reaction is faster, one with ∆G‡ = +45...Ch. 6.10 - Prob. 13PCh. 6.SE - Prob. 14VCCh. 6.SE - Prob. 15VCCh. 6.SE - Prob. 16VCCh. 6.SE - Look at the following energy diagram: (a) Is...Ch. 6.SE - Look at the following energy diagram for an...Ch. 6.SE - What is the difference between a transition state...Ch. 6.SE - Prob. 20EDRMCh. 6.SE - Prob. 21EDRMCh. 6.SE - Draw an energy diagram for a two-step exergonic...Ch. 6.SE - Draw an energy diagram for a reaction with keq =...Ch. 6.SE - The addition of water to ethylene to yield ethanol...Ch. 6.SE - When isopropylidenecyclohexane is treated with...Ch. 6.SE - Prob. 26EDRMCh. 6.SE - Draw the electron-pushing mechanism for each...Ch. 6.SE - Draw the complete mechanism for each polar...Ch. 6.SE - Prob. 29EDRMCh. 6.SE - Identify the functional groups in the following...Ch. 6.SE - Identify the following reactions as additions,...Ch. 6.SE - Identify the likely electrophilic and nucleophilic...Ch. 6.SE - For each reaction below identify the electrophile...Ch. 6.SE - Prob. 34APCh. 6.SE - Follow the flow of electrons indicated by the...Ch. 6.SE - Prob. 36APCh. 6.SE - Prob. 37APCh. 6.SE - Despite the limitations of radical chlorination of...Ch. 6.SE - Prob. 39APCh. 6.SE - Answer question 6-39 taking all stereoisomers into...Ch. 6.SE - Prob. 41APCh. 6.SE - Prob. 42APCh. 6.SE - Prob. 43APCh. 6.SE - The reaction of hydroxide ion with chloromethane...Ch. 6.SE - Prob. 45APCh. 6.SE - Ammonia reacts with acetyl chloride (CH3COCl) to...Ch. 6.SE - The naturally occurring molecule α-terpineol is...Ch. 6.SE - Prob. 48APCh. 6.SE - Prob. 49APCh. 6.SE - Draw the structures of the two carbocation...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- (a) Based on what you know about the relative stabilities of alkyl cations and benzylic cations, predict the product of addition of HBr to 1-phenylpropene.(b) Propose a mechanism for this reaction.arrow_forwardPredict the products formed when CH3CH2¬C‚C≠- Na+ reacts with the following compounds.(a) ethyl bromide (b) tert-butyl bromide(c) formaldehydearrow_forward10. Compound X (C4H9Br) reacts by heating with NaOH in H2O to form Y. The compound Y then undergoes acid catalysed hydration by H2SO, in 180°C to form 2-methyl prop-1-ene. (e) Determine the structure of X and Y. (f) Predict a MAJOR product when compound Y reacts with H2SO4 in 140 C. (g) Draw a structural isomer of X. Name the isomer using IUPAC nomenclature. (h) Describe a chemical test to distinguish between compound Y and 1-butanol.arrow_forward
- A key step in the hydrolysis of acetamide in aqueous acid proceeds by nucleophilic addition of * OH (a) H3O* to CH3Ĉ NH2 (b) H2O to CH3ČNH2 + OH +OH (c) H3O* to CH,ČNH2 (d) HO¯ to CH3CNH2arrow_forwardWhat is the major Organic product of the following reaction? (d) O ZEU OH CH₂N₂ CH; (b) (e) NH₂ NH₂ C (0) OCH, CH;arrow_forwardPredict the products formed when CH3CH2¬C‚C≠- Na+ reacts with the following compounds.(a) ethyl bromidearrow_forward
- (a) How many Stereoisomers are possible for 9,10- dibromoexadecanoic acid?(b) Addition of bromine to palmitoleic acid primarily yields a set of enantiomers, (±) -three-9,10-dibromohexadecanoic acid. The addition of bromine is an anti-addition to the double bond (ie, it appears to occur through the intermediary of the bromonium ion). Taking into account the stereochemistry of the cis double bond of palmitoleic acid and the stereochemistry of adding bromine,Write a three-dimensional structure for (±) -three-9,10-dibromohexadecanoic acid!arrow_forwardThe rate constant for the uncatalyzed reaction of two molecules of glycine ethyl ester to form glycylglycine ethyl ester is 0.6 M-1s-1. In the presence of Co2+, the rate constant is 1.5 x 106 M-1s-1. What rate enhancement does the catalyst provide?arrow_forward(b) 3-methyl-2-butanol reacts with concentrated sulphuric acid to form 2-methyl-2- butene. Write the mechanism for the reaction.arrow_forward
- A chemist synthesized compound X as a racemic mixture. When the ketone group in X was enzymatically reduced to the corresponding alcohol, a 100% yield was obtained of the product shown below. Choose the statement that best describes this result. ОН enzyme C;H1 `OCH,CH; pH 4.0 C3H1 `OCH,CH3 ОН ÕH X (racemic) (100% yield) One enantiomer of compound X reacts quickly with the enzyme. The other enantiomer of compound X is unreactive, but rapidly equilibrates with the reactive enantiomer under the reaction conditions. Since compound X was racemic, it makes sense that only a single product was obtained. O The product is a meso compound, so either enantiomer of compound X gives the same product. One enantiomer of compound X reacts quickly with the enzyme, while the other enantiomer of compound X remains unchanged.arrow_forwardFollowing is a balanced equation for bromination of toluene.(a) Using the values for bond dissociation enthalpies given in Appendix 3,calculate ∆H0for this reaction.(b) Propose a pair of chain propagation steps and show that they add up to theobserved reaction.(c) Calculate ∆H0for each chain propagation step.(d) Which propagation step is rate-determininarrow_forward5. Consider the synthesis of 2-butanone from butyne: Hg2+ CH3CH,-C=C–H CH3CH, Ĉ -CH3 H3o* (i) Draw the structure of the compound D. (ii) Compound D isomerizes to form 2-butanone. What is this isomeric process called? (iii) Use the mechanism to show the conversion of compound D to 2-butanone.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
General Chemistry | Acids & Bases; Author: Ninja Nerd;https://www.youtube.com/watch?v=AOr_5tbgfQ0;License: Standard YouTube License, CC-BY