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(a)
Interpretation:The stereocenter in thalidomide should be identified.
Concept introduction:Chiral carbon is any stereocenter attached to four different alkyl substituents. It is also known as stereocenter. If any two of the substituent happen to be similar the center is regarded as achiral. However, the most essential criteria that help to distinguish a chiral or non-chiral system ispresence of any symmetry element. If any plane center or axis of symmetry is identified it makes molecule achiral and optically inactive.
Thalidomide was originally taken as sedative against morning sickness; while one of its enantiomers was successful as sedative, other enantiomer caused certain birth defects.
(b)
Interpretation:Two enantiomers in thalidomide should be drawn and labeled.
Concept introduction:In order to assign absolute configuration of R and S, Cahn − Ingold − Prelog rules are used and the first step is to assign the priority order on the basis of
The Fischer projection is written along with the priorities assigned and groups are interchanged between adjacent places so as to obtain lowest priority group at the bottom or lowest priority.
If the groups now are arranged are read from highest towards least in clockwise fashion the R is assigned to the stereocenter, if the rotation is anticlockwise the S is assigned at the configuration.
(c)
Interpretation: The relevant hydrogen that shows acidic properties should be identified in thalidomide.
Concept introduction:Thalidomide was originally taken as sedative against morning sickness; while one of its enantiomer was successful as sedative, other enantiomer caused certain birth defects. The two enantiomers of thalidomide are as follows:
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Chapter 5 Solutions
Organic Chemistry: Structure and Function
- Determine the pH of solution of HC3H5O2 By constructing an ICE table writing the equilibrium constant expression, and using this information to determine the pH. The Ka of HC3H5O2 is 1.3 x 10-5arrow_forwardDetermine if the following salt is neutral, acidic or basic. If acidic or basic, write the appropriate equilibrium equation for the acid or base that exists when the salt is dissolved in aqueous solution. If neutral, simply write only NR. Be sure to include the proper phases for all species within the reaction LiNO3arrow_forwardAn unknown weak acid with a concentration of 0.410 M has a pH of 5.600. What is the Ka of the weak acid?arrow_forward
- (racemic) 19.84 Using your reaction roadmaps as a guide, show how to convert 2-oxepanone and ethanol into 1-cyclopentenecarbaldehyde. You must use 2-oxepanone as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way. & + EtOH H 2-Oxepanone 1-Cyclopentenecarbaldehydearrow_forwardR₂ R₁ R₁ a R Rg Nu R₂ Rg R₁ R R₁₂ R3 R R Nu enolate forming R₁ R B-Alkylated carbonyl species or amines Cyclic B-Ketoester R₁₁ HOB R R₁B R R₁₂ B-Hydroxy carbonyl R diester R2 R3 R₁ RB OR R₂ 0 aB-Unsaturated carbonyl NaOR Aldol HOR reaction 1) LDA 2) R-X 3) H₂O/H₂O ketone, aldehyde 1) 2°-amine 2) acid chloride 3) H₂O'/H₂O 0 O R₁ R₁ R R₁ R₁₂ Alkylated a-carbon R₁ H.C R₁ H.C Alkylated methyl ketone acetoacetic ester B-Ketoester ester R₁ HO R₂ R B-Dicarbonyl HO Alkylated carboxylic acid malonic ester Write the reagents required to bring about each reaction next to the arrows shown. Next, record any regiochemistry or stereochemistry considerations relevant to the reaction. You should also record any key aspects of the mechanism, such as forma- tion of an important intermediate, as a helpful reminder. You may want to keep track of all reactions that make carbon-carbon bonds, because these help you build large molecules from smaller fragments. This especially applies to the reactions in…arrow_forwardProvide the reasonable steps to achieve the following synthesis.arrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning