(a)
Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.
Concept Introduction:
An azide is converted into an
To find: Draw the structures of 2 and 3
Do hydrogenation on an azide
(b)
Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.
Concept Introduction:
An enamine is an unsaturated compound derived by the reaction of an
To find: Provide an acid-catalyzed mechanism for the conversion of 3 to 4
Do protonation for imine
(c)
Interpretation: The structures of 2 and 3, an acid-catalyzed mechanism for the conversion of 3 to 4 and the reasons for the equilibrium favor enamine 4 over imine 3 have to be found for the given reactions.
Concept Introduction:
An enamine is an unsaturated compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by loss of H2O. The word "enamine" is derived from the affix en-, used as the suffix of alkene, and the root amine. This can be compared with enol, which is a functional group containing both alkene (en-) and alcohol (-ol). Enamines are considered to be nitrogen analogs of enols. If one of the nitrogen substituents is a hydrogen atom, H, it is the tautomeric form of an imine. This usually will rearrange to the imine; however there are several exceptions (such as aniline). The enamine-imine tautomerism may be considered analogous to the keto-enol tautomerism. In both cases, a hydrogen atom switches its location between the heteroatom (oxygen or nitrogen) and the second carbon atom. Enamines are both good nucleophiles and good bases.
To find: Get the reasons for the equilibrium favor enamine 4 over imine 3
Explain the conjugation
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Chapter 23 Solutions
Organic Chemistry, Binder Ready Version
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- The following reactions are NOT ordered in the way in which they occur. Reaction 1 PhO-OPh Reaction 2 Ph-O -CH₂ heat 2 *OPh Pho -CH2 Reaction 3 Ph-O ⚫OPh + -CH₂ Reaction 4 Pho Pho + H₂C OPh + CHOPh H₂C -CH₂ Reactions 1 and 3 Reaction 2 O Reaction 3 ○ Reactions 3 and 4 ○ Reactions 1 and 2 Reaction 4 ○ Reaction 1arrow_forwardSelect all possible products from the following reaction: NaOH H₂O a) b) ОН HO O HO HO e) ОН f) O HO g) h) + OHarrow_forward3. Draw diagrams to represent the conjugation in these molecules. Draw two types of diagram: a. Show curly arrows linking at least two different ways of representing the molecule b. Indicate with dotted lines and partial charges (where necessary) the partial double bond (and charge) distribution H₂N* H₂N -NH2arrow_forward
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