CAREY: ORGANIC CHEMISTRY
10th Edition
ISBN: 9781260364002
Author: VALUE EDITION
Publisher: MCG CUSTOM
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 16, Problem 34P
Interpretation Introduction
Interpretation:
The correct enantiomer of
Concept introduction:
The alcohols on reaction with
As the hydroxyl group of alcohol acts as a nucleophile, there is no change in configuration of alcohol and tosylate (
The thiol can be prepared from
The
Expert Solution & Answer
![Check Mark](/static/check-mark.png)
Want to see the full answer?
Check out a sample textbook solution![Blurred answer](/static/blurred-answer.jpg)
Students have asked these similar questions
Describe how 3-methyl-1-phenyl-3-pentanol can be prepared from benzene. You can use any inorganic reagents and solvents, and any organic reagents provided they contain no more than two carbons.
When trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone.
Why doesn’t the cis isomer yield the oxide?
Dimethyl disulfide, CH,S–SCH3, found in the vaginal secretions of
female hamsters, acts as a sexual attractant for the male hamster. Write
an equation for its synthesis from methanethiol.
Chapter 16 Solutions
CAREY: ORGANIC CHEMISTRY
Ch. 16.2 - Prob. 1PCh. 16.2 - Prob. 2PCh. 16.4 - Prob. 3PCh. 16.5 - Prob. 4PCh. 16.5 - Give the structures, including stereochemistry,...Ch. 16.5 - Prob. 6PCh. 16.7 - Prob. 7PCh. 16.8 - Prob. 8PCh. 16.8 - Prob. 9PCh. 16.9 - Predict the principal organic product of each of...
Ch. 16.9 - Prob. 11PCh. 16.10 - Prob. 12PCh. 16.11 - Prob. 13PCh. 16.12 - Prob. 14PCh. 16.12 - Prob. 15PCh. 16 - Write chemical equations, showing all necessary...Ch. 16 - Write chemical equations, showing all necessary...Ch. 16 - Which of the isomeric C5H12O alcohols can be...Ch. 16 - Prob. 19PCh. 16 - Write equations showing how 1-phenylethanol could...Ch. 16 - Write equations showing how 2-phenylethanol could...Ch. 16 - Prob. 22PCh. 16 - Show how each of the following compounds can be...Ch. 16 - Prob. 24PCh. 16 - Write the structure of the principal organic...Ch. 16 - Prob. 26PCh. 16 - Prob. 27PCh. 16 - Prob. 28PCh. 16 - Prob. 29PCh. 16 - Prob. 30PCh. 16 - (a) The cis isomer of 3-hexen-1-ol...Ch. 16 - Prob. 32PCh. 16 - Complete each of the following equations by...Ch. 16 - Prob. 34PCh. 16 - Prob. 35PCh. 16 - A diol (C8H18O2) does not react with periodic...Ch. 16 - Identify the compound C8H10O on the basis of its...Ch. 16 - dentify each of the following C4H10O isomers on...Ch. 16 - Prob. 39PCh. 16 - A compound C6H14O has the spectrum shown in Figure...Ch. 16 - Prob. 41DSPCh. 16 - Prob. 42DSPCh. 16 - Prob. 43DSPCh. 16 - Prob. 44DSPCh. 16 - Prob. 45DSPCh. 16 - Prob. 46DSPCh. 16 - Prob. 47DSP
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
- Account for the fact that treating propenoic acid (acrylic acid) with HCl gives only 3-chloropropanoic acid.arrow_forwardIn the chemical synthesis of DNA and RNA, hydroxyl groups are normally converted to triphenylmethyl (trityl) ethers to protect the hydroxyl group from reaction with other reagents. Triphenylmethyl ethers are stable to aqueous base but are rapidly cleaved in aqueous acid. (a) Why are triphenylmethyl ethers so readily hydrolyzed by aqueous acid? (b) How might the structure of the triphenylmethyl group be modified to increase or decrease its acid sensitivity?arrow_forwardDibenzalpropanone is a compound that can absorb UV rays and can be used as a sunscreen. Write down the reagents used to synthesize the compound dibenzalpropanone.arrow_forward
- Reaction of 1-butanol with periodane gives Butanal Propanoic acid 2-Butanone Butanoic acid as the major product.arrow_forwardPredict the products formed when cyclohexanone reacts with the following reagents.(a) CH3NH2, Harrow_forwardCompound A and compound B both have molecular formula C6H12. Both compounds produce epoxides when treated with a peroxy acid (RCO3H). The epoxide resulting from compound A was treated with aqueous acid (H3O+) and the resulting diol has no chiral centers. Identify the two possible structures for compound A (enter two numbers separated by commas with no spaces, e.g. "1,2") The epoxide resulting from compound B was treated with (H3O*) and the resulting diol was a meso compound. Identify compound B 2 3 potn 7 1 5 6 4 8arrow_forward
- The following molecule belongs to a class of compounds called enediols; each carbon of the double bond carries an-OH group. Draw structural formulas for the a-hydroxyketone and the a-hydroxyaldehyde with which this enediol is in equilibrium. CH-OH a-Hydroxyaldehyde = C-OH= a -Hydroxyketone ČH3 An enediolarrow_forwardPredict the products formed when cyclohexanecarbaldehyde reacts with the following reagents.(a) PhMgBr, then H3O+ (b) Tollens reagent (c) semicarbazide and weak acid(d) excess ethanol and acid (e) propane-1,3-diol, H+ (f) zinc amalgam and dilute hydrochloric acidarrow_forwardWhich one of the following combinations give ethoxy benzene? A Sodium ethoxide and chlorobenzene Ethyl bromide and sodium phenoxide Ethanol and benzene Ethyl chloride and phenolarrow_forward
- The ketone 2-heptanone has been identified as contributing to the odor of a number of dairy products, including condensed milk and cheddar cheese. Describe the synthesis of 2-heptanone from acetylene and any necessary organic and inorganic reagents.arrow_forwardWhat reactions and reagents can be used to make phenol from benzene if electrophilic aromatic substitution reactions are excluded and benzene is the only source of carbon?arrow_forwardEthyl butyrate, CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring.It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l). The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0% yield. How many grams would be produced from 8.50 gof butanoic acid and excess ethanol? Express your answer in grams to three significant figures.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305580350/9781305580350_smallCoverImage.gif)
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
How to Design a Total Synthesis; Author: Chemistry Unleashed;https://www.youtube.com/watch?v=9jRfAJJO7mM;License: Standard YouTube License, CC-BY