
Organic Chemistry - With Access (Custom)
9th Edition
ISBN: 9781337031745
Author: McMurry
Publisher: Cengage
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 solution
Students have asked these similar questions
Can u help me figure out the reaction mechanisms for these, idk where to even start
Hi, I need your help with the drawing, please. I have attached the question along with my lab instructions. Please use the reaction from the lab only, as we are not allowed to use outside sources. Thank you!
Hi, I need your help i dont know which one to draw please. I’ve attached the question along with my lab instructions. Please use the reaction from the lab only, as we are not allowed to use outside sources. Thank you!
Chapter 28 Solutions
Organic Chemistry - With Access (Custom)
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
- 5. Write the formation reaction of the following complex compounds from the following reactants: 6. AgNO₃ + K₂CrO₂ + NH₄OH → 7. HgNO₃ + excess KI → 8. Al(NO₃)₃ + excess NaOH →arrow_forwardIndicate whether the product formed in the reaction exhibits tautomerism. If so, draw the structure of the tautomers. CO₂C2H5 + CH3-NH-NH,arrow_forwardDraw the major product of this reaction N-(cyclohex-1-en-1-yl)-1-(pyrrolidino) reacts with CH2=CHCHO, heat, H3O+arrow_forward
- Draw the starting material that would be needed to make this product through an intramolecular Dieckmann reactionarrow_forwardDraw the major product of this reaction. Nitropropane reacts + pent-3-en-2-one reacts with NaOCH2CH3, CH3CHOHarrow_forwardIndicate whether the product formed in the reaction exhibits tautomerism. If so, draw the structure of the tautomers. OC2H5 + CoHs-NH-NH,arrow_forward
- Explain how substitutions at the 5-position of barbituric acid increase the compound's lipophilicity.arrow_forwardExplain how substitutions at the 5-position of phenobarbital increase the compound's lipophilicity.arrow_forwardName an interesting derivative of barbituric acid, describing its structure.arrow_forward
- Briefly describe the synthesis mechanism of barbituric acid from the condensation of urea with a β-diketone.arrow_forwardGiven the hydrazones indicated, draw the structures of the enamines that can be formed. Indicate the most stable enamine (explain). C6H5 C6H5 H C6H5 Harrow_forward4. Propose a Synthesis for the molecule below. You may use any starting materials containing 6 carbons or less (reagents that aren't incorporated into the final molecule such as PhзP do not count towards this total, and the starting material can have whatever non-carbon functional groups you want), and any of the reactions you have learned so far in organic chemistry I, II, and III. Your final answer should show each step separately, with intermediates and conditions clearly drawn.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