ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 11, Problem 11.32P
Interpretation Introduction
Interpretation: A stepwise mechanism for the acid-catalyzed conversion of enamine X to imine Y is to be drawn.
Concept Introduction: The
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
(b) Draw a stepwise mechanism for the following transformation from A to B. This reaction is one of the key
steps in a synthesis of lysergic acid diethyl amide (aka LSD).
CI
A
CH ₂
AIC13
B
CH₂
several steps away
from
lysergic acid diethyl amide
(LSD)
The Stork reaction is a condensation reaction between an enamine donor and an a,ß-unsaturated carbonyl acceptor. The overall reaction consists of a
three-step sequence of
1. formation of an enamine from a ketone,
2. Michael addition to an a,ß-unsaturated carbonyl compound, and
3. hydrolysis of the enamine in dilute acid to regenerate the ketone.
Consider the Stork reaction between acetophenone and propenal.
1 Draw the structure of the product of the enamine formed between acetophenone and morpholine.
90-85
?
What is the major Hofmann elimination product formed from each amine?
Chapter 11 Solutions
ORGANIC CHEMISTRY
Ch. 11 - Problem 11.1 Neopheliosyne B is a novel acetylenic...Ch. 11 - Give the IUPAC name for each compound.Ch. 11 - Give the structures corresponding to each of the...Ch. 11 - Prob. 11.4PCh. 11 - Prob. 11.5PCh. 11 - Which bases can deprotonate acetylene? The pKa...Ch. 11 - Draw the organic products formed when each alkyne...Ch. 11 - Draw additional resonance structures for each...Ch. 11 - Problem 11.9 Draw the products formed when is...Ch. 11 - Explain the following result. Although alkenes...
Ch. 11 - Problem 11.11 Draw the keto tautomer of each...Ch. 11 - Prob. 11.12PCh. 11 - a Draw two different enol tautomers of...Ch. 11 - Prob. 11.14PCh. 11 - Problem 11.15 Draw the organic products formed in...Ch. 11 - Problem 11.16 What acetylide anion and alkyl...Ch. 11 - Problem. 11.17 Show how , and can be used to...Ch. 11 - Prob. 11.18PCh. 11 - Draw the products of each reaction. a. b.Ch. 11 - Prob. 11.20PCh. 11 - Problem 11.21 Use retrosynthetic analysis to show...Ch. 11 - Prob. 11.22PCh. 11 - Give the IUPAC name for each compound. a. b.Ch. 11 - Prob. 11.24PCh. 11 - 11.25 Answer the following questions about...Ch. 11 - 11.26 Give the IUPAC name for each alkyne.
a. ...Ch. 11 - Prob. 11.27PCh. 11 - Which of the following pairs of compounds...Ch. 11 - Prob. 11.29PCh. 11 - 11.30 How is each compound related to A? Choose...Ch. 11 - Prob. 11.31PCh. 11 - Prob. 11.32PCh. 11 - 11.33 Draw the products formed when is treated...Ch. 11 - What reagents are needed to convert (CH3CH2)3CCCH...Ch. 11 - Prob. 11.35PCh. 11 - 11.36 What alkynes give each of the following...Ch. 11 - 11.37 What alkyne gives each compound as the only...Ch. 11 - 11.38 Draw the organic products formed in each...Ch. 11 - 11.39 Draw the structure of compounds A-E in the...Ch. 11 - Prob. 11.40PCh. 11 - Prob. 11.41PCh. 11 - 11.42 What reactions are needed to convert alcohol...Ch. 11 - Prob. 11.43PCh. 11 - Prob. 11.44PCh. 11 - 11.45 Explain the following statement. Although ...Ch. 11 - 11.46 Tautomerization in base resembles...Ch. 11 - 11.47 Draw a stepwise mechanism for each...Ch. 11 - Prob. 11.48PCh. 11 - Prob. 11.49PCh. 11 - 11.50 What acetylide anion and alkyl halide are...Ch. 11 - 11.51 Synthesize each compound from acetylene. You...Ch. 11 - 11.52 Devise a synthesis of each compound using ...Ch. 11 - Prob. 11.53PCh. 11 - Prob. 11.54PCh. 11 - 11.55 Devise a synthesis of the ketone, , from ...Ch. 11 - 11.56 Devise a synthesis of each compound using ...Ch. 11 - Prob. 11.57PCh. 11 - Prob. 11.58PCh. 11 - 11.59 N-Chlorosuccinimide (NCS) serves as a source...Ch. 11 - 11.60 Draw a stepwise mechanism for the following...Ch. 11 - 11.61 Draw a stepwise mechanism for the following...Ch. 11 - Prob. 11.62PCh. 11 - 11.63 Write a stepwise mechanism for each of the...Ch. 11 - Prob. 11.64PCh. 11 - 11.65 Explain why an optically active solution of ...
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
- Write the mechanism for the following reactions: 1. the acid-catalyzed hydrolysis of an imine to a carbonyl compound and a primary amine 2. the acid-catalyzed hydrolysis of an enamine to a carbonyl compound and a secondary amine a. How do the two mechanisms differ?arrow_forwardAspirin is an anti-inflammatory agent because it inhibits the conversion of arachidonic acid to prostaglandins by the transfer of its acetyl group (CH3CO−) to an OH group at the active site of an enzyme. This reaction, called transesterification, results in the conversion of one ester to another by a nucleophilic acyl substitution reaction. Draw a stepwise mechanism for the given transesterification.arrow_forward4. WHAT ARE IMINES? HOW ARE THEY FORMED? 5. WHAT IS GRIGNARD REACTION? WHAT CONSTITUTES A GRIGNARD REAGENT? 6. WHAT IS KETO-ENOL TAUTOMERIZATION?arrow_forward
- Which carbonyl groups in the anticancer drug Taxol will undergo nucleophilic addition, and which will undergo nucleophilic substitution?arrow_forwardMatch each reagent to the product that it forms. Multiple reagents may form the same product. нох Reagent Reagents SOCI2, pyridine: C CISO2CH3, pyridine: E HCI: A PCI 3: A A) B) "It "ft "bl H₂O D) E) F) پہلے علی علیہarrow_forwardDraw the products formed when p-methylaniline (p-CH3C6H4NH2) istreated with following reagent. NaNO2, HClarrow_forward
- How imines and enamines are converted back to carbonyl compounds by hydrolysis with mild acid ?arrow_forward18) The following reaction undergoes three distinct steps: imine formation, electrophilic aromatic substitution, and decarboxylation. Draw each of the intermediates from each of these three steps as well as the final product. BS NH₂ OH heatarrow_forwardWhich functional group has the maximum reactivity toward nucleophilic attack? a) acid chloride b) ketone c) ester d) amidearrow_forward
- Rank the following esters in order of decreasing reactivity in the first slow step of a nucleophilic acyl substitution reaction (formation of the tetrahedral intermediate):Rank the same esters in order of decreasing reactivity in the second slow step of a nucleophilic acyl substitution reaction (collapse of the tetrahedral intermediate).arrow_forward1) Draw AND name the product that would result upon treatment of R-3-methylheptanal with Excess aqueous sodium hydroxide together with excess chlorine. 2) Draw AND name the product that would result upon treatment of R-3-methylheptanal with Bromine in acetic acid. 3) Draw the product that would result upon treatment of R-3-methylheptanal with1-butanamine using a Dean Stark trap. Draw the product and then react the product with lithium aluminum hydride followed by hydrochloric acid. Give a complete mechanism. 4) Draw the product that would result upon treatment of R-3-methylheptanal with Disopropyl amine using a Dean Stark trap. Draw the product and then react the product with hydrogen gas in the presence of a platinum catalyst.arrow_forwardThe Stork reaction is a condensation reaction between an enamine donor and an a,ẞ-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of 1. formation of an enamine from a ketone. 2. Michael addition to an α,ß-unsaturated carbonyl compound, and 3. hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between cyclohexanone and propenal. Draw the structure of the product of the enamine formed between cyclohexanone and dimethylamine. ચર્ચ F Correct HC, CH3 ChemDoodle 2 Draw the structure of the Michael addition product. ChemDoodle Jn (F 106 Correctarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning