When an alcohol and an aldehyde exist in the same compound, this compound is in equilibrium with what is called a " cyclic hemiacetal." The cyclic hemiacetal is favored when a 5- or 6- membered ring is formed. As shown below, this cyclic hemiacetal is formed via a new bond formation between the oxygen of the alcohol and the carbon of the C=O double bond. (We will look at this more specifically in Orgo II). H. 1 3 H G H 1) BH3-THF; 2) H₂O2, NaOH 1) 03; 2) DMS cold, dilute KMnO4,NaOH new bond formed 1) Hg(OAc)2, H₂O 2) NaBH4 1 With this in mind, which reagents will produce an alcohol from starting material G that will then cyclize to product cyclic hemiacetal H? O-H 5 4 3 a "cycli hemiacetal" H OH

When an alcohol and an aldehyde exist in the same compound, this compound is in equilibrium with what is called a " cyclic hemiacetal." The cyclic hemiacetal is favored when a 5- or 6- membered ring is formed. As shown below, this cyclic hemiacetal is formed via a new bond formation between the oxygen of the alcohol and the carbon of the C=O double bond. (We will look at this more specifically in Orgo II). H. 1 3 H G H 1) BH3-THF; 2) H₂O2, NaOH 1) 03; 2) DMS cold, dilute KMnO4,NaOH new bond formed 1) Hg(OAc)2, H₂O 2) NaBH4 1 With this in mind, which reagents will produce an alcohol from starting material G that will then cyclize to product cyclic hemiacetal H? O-H 5 4 3 a "cycli hemiacetal" H OH

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter17: Alcohols And Phenols

Section17.SE: Something Extra

Problem 71AP: A problem often encountered in the oxidation of primary alcohols to acids is that esters are...

See similar textbooks

Similar questions

We have covered several oxidants that use a multi-valent atom (Cr, Cl, S, or I) as theiractive species, going from a higher oxidation state before the oxidation to a lower oxidation state after oxidizing the alcohol. Draw the structure of the following atoms, beforeand after the oxidation of an alcohol to a ketone or aldehyde. How many bonds to oxygendoes each atom have before and after the oxidation?(a) the Cr in chromic acid (b) the Cl in sodium hypochlorite(c) the S in the Swern oxidation (d) the I in the DMP reagent(e) the carbinol C in the alcohol that is oxidized
Which of the following ketones would be the most soluble in water? (Hìnt: Remember the relation between the number of carbons in aldehydes and ketones and their solubility in water.) O CH3-CH2-CH2-CO-CH3 O CH3-CH2-CH2-CO-CH2-CH2-CH3 O CH3-CO-CH2-CH3 O CH3-CO-CH2-CH2-CH2-CH3
The addition of water to aldehydes and ketones occurs rapidly, although it is not thermodynamically favored. What would be the product for the reaction above? Hint: Think of the self-ionization of water and the polarity of the carbonyl group.
A problem often encountered in the oxidation of primary alcohols to acids is that esters are sometimes produced as by-products. For example, oxidation of ethanol yields acetic acid and ethyl acetate: Propose a mechanism to account for the formation of ethyl acetate. Take into account the reversible reaction between aldehydes and alcohols:
Which of (a)-(d) is the correct IUPAC name of the following compound? * HO O 3-methyl-1-phenyl-1-pentanol ○ 3-methyl-5-phenyl-5-pentanol ○ 3-methyl-1-benzene-1-pentanol O 1-phenyl-1-hexanol
6. Show how the following alcohols below can be distinguished. a) butanol and 2- butanol b) 2-propanol and 3- hexanol
We have covered several oxidants that use a multi-valent atom (Cr, Cl, S, or I) as their active species, going from a higher oxidation state before the oxidation to a lower oxidation state after oxidizing the alcohol. Draw the structure of the following atoms, before and after the oxidation of an alcohol to a ketone or aldehyde. How many bonds to oxygen does each atom have before and after the oxidation? (a) the I in the DMP reagent (b) the carbinol C in the alcohol that is oxidized
A) Provide four different ways that 2-methylpropanal could be made from an alkene, an alcohol, an ester and an acetal in a single step. an alkene H an alcohol 2-methylpropanal an ester an acetal
How do I go by this problem?
Phenol and other derivatives with a single hydroxyl group on the aromatic ring are not easily oxidized to form a ketone. Why is this? Select all that apply: O Phenol is a secondary alcohol; secondary alcohols do not oxidize. O The carbon that the hydroxyl group is attached to in phenol does not have a hydrogen attached. Forming a double bond between the oxygen and the carbon would require breaking up the stable aromatic ring. Phenol is a tertiary alcohol, which does not oxidize.
Which of the following is correct about thioethers? They are more reactive than their corresponding ethers. They are partially responsible for “morning breath.” They are organic compounds in which a sulfur is bonded to two carbon atoms by a single bond. All of the above
Assign IUPAC names to the following ketones: || a. CH,CH,CH,CH,CH, -C-CH, || b. CH,CHCH-C-CHCH, CH,CH, CH,CH, C. H,C CH;-C-CH– CH, 一 CH; d.