(a)
Interpretation: The structure of proline has to be drawn:
Concept Introduction:
Enamine formation:
Example for the formation of enamine is shown here:
In enamines, the lone pair of nitrogen will be in resonance with the adjacent
Retro synthetic analysis:
It is the analysis of the synthetic starting materials for a given compound through its precursors or fragments which are known as synthons. The synthons can be obtained by logical cleavage of the
Retro analysis for enamine formation:
The retro analysis of enamine reveals that the starting material of an enamine will be a secondary amine and a carbonyl compound.
Example:
(b)
Interpretation: The plausible mechanism for the reaction between compounds 1 and 2 has to be drawn.
Concept Introduction:
Enamine formation:
Aldehyde or ketone reacts with a secondary amine and forms enamine in mildly acidic conditions.
Example for the formation of enamine is shown here:
In enamines, the lone pair of nitrogen will be in resonance with the adjacent

Want to see the full answer?
Check out a sample textbook solution
Chapter 19 Solutions
ORGANIC CHEMISTRYPKGDRL+MLCRL MDL
- Q2: Explain why epoxides that react in an SN1 manner will not show any stereochemical inversion in the product. Q3: Rationalize why Alcohol B will react under the indicated reaction conditions, but Alcohol A will not. A ☑ OH B OH PBr3 R-Brarrow_forwardQ1: Predict the major organic product(s) of the following reactions. Include stereochemistry when necessary. Write NR if no reaction, try to explain. 1.) LDA, THF 2.) СОН CI OH H2SO4, heat OH m...... OH 1.) PCC, CH2Cl2 2.) CH3CH2MgBr, THF 3.) H3O+ 4.) TsCl, pyr 5.) tBuOK, tBuOH 1.) SOCI 2, CHCI 3 2.) CH3CH2ONA, DMF OH 1.) HBr 2.) Mg, THF 3.) H₂CO, THE 4.) H3O+ OH NaH, THFarrow_forwardWhat is the stepwise mechanism for this reaction?arrow_forward
- Draw the major product of this reactionarrow_forwardPlease provide the IUPAC name for the compound shown herearrow_forwardProblem 6-29 Identify the functional groups in the following molecules, and show the polarity of each: (a) CH3CH2C=N CH, CH, COCH (c) CH3CCH2COCH3 NH2 (e) OCH3 (b) (d) O Problem 6-30 Identify the following reactions as additions, eliminations, substitutions, or rearrangements: (a) CH3CH2Br + NaCN CH3CH2CN ( + NaBr) Acid -OH (+ H2O) catalyst (b) + (c) Heat NO2 Light + 02N-NO2 (+ HNO2) (d)arrow_forward
- Predict the organic product of Y that is formed in the reaction below, and draw the skeletal ("line") structures of the missing organic product. Please include all steps & drawings & explanations.arrow_forwardPlease choose the best reagents to complete the following reactionarrow_forwardProblem 6-17 Look at the following energy diagram: Energy Reaction progress (a) Is AG for the reaction positive or negative? Label it on the diagram. (b) How many steps are involved in the reaction? (c) How many transition states are there? Label them on the diagram. Problem 6-19 What is the difference between a transition state and an intermediate? Problem 6-21 Draw an energy diagram for a two-step reaction with Keq > 1. Label the overall AG°, transition states, and intermediate. Is AG° positive or negative? Problem 6-23 Draw an energy diagram for a reaction with Keq = 1. What is the value of AG° in this reaction?arrow_forward
- Problem 6-37 Draw the different monochlorinated constitutional isomers you would obtain by the radical chlorination of the following compounds. (b) (c) Problem 6-39 Show the structure of the carbocation that would result when each of the following alkenes reacts with an acid, H+. (a) (b) (c)arrow_forwardPlease draw the major product of this reaction. Ignore inorganic byproducts and the carboxylic side productarrow_forwardPlease draw the major product of this reaction.arrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY





