ORGANIC CHEMISTRY-EBOOK>I<
9th Edition
ISBN: 9781305084414
Author: McMurry
Publisher: INTER CENG
expand_more
expand_more
format_list_bulleted
Question
Chapter 28.7, Problem 12P
Interpretation Introduction
Interpretation:
Determine the mechanism for the cleavage of β-cyanoethyl protective group by using aqueous ammonia and state the type of occurring reaction.
Concept introduction:
The cleavage of β-cyanoethyl protective group occurs according to the β-elimination mechanism. In β-elimination mechanism, the bond β to the nucleophilic pair of electrons breaks. The elimination reaction involves the breaking of the sigma (σ) bond and the formation of new pie (π) bond. In this process a lone pair electron forms a double bond as the leaving group departs.
Given information:
The cleavage of β-cyanoethyl protective group can be done by aqueous ammonia. The by-product of this reaction is acrylonitrile.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Give the major product(s) of the following reaction.
1) H2C=CHM9B
?
2) H30+
Give the major product(s) of the following reaction.
NaNMe2
heat
reactions of esters
Comparing Hydration Products Using Two Different Methods Draw the product formed when CH3CH2C=CH is treated with each of the following sets of reagents: (a) H2O, H2SO4, HgSO4; and (b) R2BH, followed by H2O2, HO−.
What reaction conditions are needed to convert (R)-2-ethyl-2- methyloxirane to (R)-2-methylbutane-1,2-diol ?
Chapter 28 Solutions
ORGANIC CHEMISTRY-EBOOK>I<
Ch. 28.1 - Draw the full structure of the DNA dinucleotide...Ch. 28.1 - Draw the full structure of the RNA dinucleotide...Ch. 28.2 - What sequence of bases on one strand of DNA is...Ch. 28.4 - Show how uracil can form strong hydrogen bonds to...Ch. 28.4 - What RNA base sequence is complementary to the...Ch. 28.4 - From what DNA base sequence was the following RNA...Ch. 28.5 - List codon sequences for the following amino...Ch. 28.5 - List anticodon sequences on the tRNAs carrying the...Ch. 28.5 - What amino acid sequence is coded by the following...Ch. 28.5 - What is the base sequence in the original DNA...
Ch. 28.7 - Prob. 11PCh. 28.7 - Prob. 12PCh. 28.SE - Identify the following bases, and tell whether...Ch. 28.SE - Identify the following nucleotide, and tell how it...Ch. 28.SE - Amine bases in nucleic acids can react with...Ch. 28.SE - The final step in DNA synthesis is deprotection by...Ch. 28.SE - The final step in the metabolic degradation of...Ch. 28.SE - One of the steps in the biosynthesis of a...Ch. 28.SE - One of the steps in the metabolic degradation of...Ch. 28.SE - One of the steps in the biosynthesis of uridine...Ch. 28.SE - Human brain natriuretic peptide (BNP) is a small...Ch. 28.SE - Human and horse insulin both have two polypeptide...Ch. 28.SE - The DNA of sea urchins contains about 32% A. What...Ch. 28.SE - The codon UAA stops protein synthesis. Why does...Ch. 28.SE - Which of the following base sequences would most...Ch. 28.SE - For what amino acids do the following...Ch. 28.SE - Prob. 27APCh. 28.SE - Prob. 28APCh. 28.SE - Draw the complete structure of the ribonucleotide...Ch. 28.SE - Draw the complete structure of the...Ch. 28.SE - Give an mRNA sequence that will code for the...Ch. 28.SE - Give an mRNA sequence that will code for the...Ch. 28.SE - What amino acid sequence is coded for by the...Ch. 28.SE - What amino acid sequence is coded for by the...Ch. 28.SE - Prob. 35APCh. 28.SE - Show the steps involved in a laboratory synthesis...Ch. 28.SE - Draw the structure of cyclic adenosine...Ch. 28.SE - Prob. 38AP
Knowledge Booster
Similar questions
- How to synthesize trans-2-methylcyclohexanol from cyclohexanone?arrow_forwardThe product of this reaction is a(n): H3CO OCH 3 cyanohydrin ketone aldehyde imine ester H3O+ productarrow_forwardOne frequently used method for preparing methyl esters is by reaction of carboxylic acids with diazomethane, CH2N2. The reaction occurs in two steps: (l) protonation of diazomethane by the carboxylic acid to yield methyldiazonium ion, CH3N2+, plus a carboxylate ion; and (2) reaction of the carboxylate ion with CH3N2+. (a) Draw two resonance structures of diazomethane, and account for step 1. (b) What kind of reaction occurs in step 2?arrow_forward
- Recalling the reactions of alcohols from Chapter 10, show how to synthesize each compound from an organohalogen compound and an oxirane, followed by a transformation of the resulting hydroxyl group to the desired oxygen-containing functional group.arrow_forwardGive the sequence of reactions that produce 2-bromo-4-ethylaniline from aniline. Draw the structures of the starting material, the first product and the final product, including all reactants used.arrow_forwardOxidation of aldehyde results in caboxylic acid in a reaction similar to this: izi. ОН (OX) || R-CH - R - OH Draw the chemicals that form when the following chemicals are oxidized a.) 3-Chloroproponal b.) Methanalarrow_forward
- Draw the principal organic product for the reaction of 2-bromohexane with lithium in diethyl ether, followed by formaldehyde in diethyl ether, and then followed by dilute acid. Click and drag to start drawing a structure. X A G Parrow_forwardProvide a mechanism for the following reaction. Show each step in your mechanism and use curved arrows to show the movement of electron pairs. Hint: the first step is a proton transfer; second step, nucleophilic attack. OCH3 H,SO4 CH;OHarrow_forwardWhat are the possible products when α-Pinene is treated with B2H6 and H2O2 + NaOH? What is the major product? What if α-Pinene is treated with peroxy acid + THF?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
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning