(a)
Interpretation:
The types of
Concept introduction:
Functional groups:
The functional group is defined as an atom or group of atoms combined in a specific manner that gives the chemical properties of the organic compound and they are the main reason for the chemical reactivity of the compound. Compounds having similar functional groups undergoes similar type of reactions.
(b)
Interpretation:
The number of chiral centres present in estrone that has to be calculated.
Concept introduction:
Chiral centre:
Chiral centre is defined as an atom bonded to four different chemical species. It is a stereo centre that holds the atom in such way that the structure may not be superimposable to its mirror image. They give optical isomerism.
(c)
Interpretation:
Structural formula for the compounds
Concept introduction:
Structural formula:
The structural formula of a compound can be defined as a graphic representation of the molecular structure showing how the atoms are arranged and the
Retrosynthetic approach:
Retrosynthetic analysis is a technique for planning a synthesis mainly for complex organic molecules where the complex target molecule is reduced into a sequence of progressively simpler structures along a pathway which ultimately leads to the identification of a simple starting molecule or easily available from which the synthesis can be developed.
During retrosynthetic analysis the target molecule is symmetrically broken down by a combination of functional group interconversion and disconnection. This disconnection is related to breaking of carbon-carbon bond of a molecule to generate simpler fragments. The complete set of disconnections and functional group interconversions for a specified target molecule is what constitutes a retrosynthetic plan.
Heck reaction:
The Heck reaction is the
(d)
Interpretation:
The pathway of converting compounds
Concept introduction:
Heck reaction:
The Heck reaction is the chemical reaction of an unsaturated halide with an alkene in presence of a base and palladium catalyst to form a substituted alkene. The reaction is as follows,
(e)
Interpretation:
The stereochemistry of compound
Concept introduction:
The Heck reaction is the chemical reaction of an unsaturated halide with an alkene in presence of a base and palladium catalyst to form a substituted alkene. The reaction is as follows,
(f)
Interpretation:
The pathway of conversion of tertiary butyl ether to acetone to form estrone from compound
Concept introduction:
Oxidation of secondary alcohol:
Oxidation of alcohol to carbonyl is very difficult as the reaction is so fast that it always ends up by giving acid. Hence for secondary alcohol to get oxidised to carbonyl selectively PCC is used.
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Organic Chemistry
- Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is closely related to that of tamoxifen. (a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and the tetrahydropyranyl (THP) group. Draw a structural formula of each group and describe the experimental conditions under which it is attached and removed. (b) Discuss the chemical logic behind the use of each blocking group in this synthesis. (c) Propose a mechanism for the conversion of D to E. (d) Propose a mechanism for the conversion of F to toremifene. (e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?arrow_forwardThe formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol intermediate and molecular bromine. The intermediate then undergoes acid-catalyzed tautomerism to form succinimide, the byproduct of the reaction. Propose a curved-arrow mechanism for the conversion of NBS into succinimide that also accounts for the formation of Br2.arrow_forwardGive mechanism asaparrow_forward
- Gamma(y)-amino butyric acid (GABA) is a neurotransmitter (a chemical that is used to send signals from one neuron to another) of the mammalian central nervous system. In order to understand how GABA works, conformationally restricted analogues, such as compound 1, have been made. During a synthesis of compound 1, compound 2 was subjected to allylic bromination using NBS and a radical initiator (AIBN) instead of light (Aust. J. Chem. 1981, 34, 2231-2236). H₂N. CH3 GABA CO₂H CH3 dddd CH3 H₂N Modify the structures given below to draw all eight possible allylic bromides that can be formed when compound 2 undergoes allylic bromination, considering all possible regiochemical and stereochemical outcomes. You can use the single bond tool to add/remove pi bonds. CH3 CO₂H CH3 solddd CH3 CH3 2 CH₂ CO₂Etarrow_forward18arrow_forwardWithout looking at a table of pKa data, rank the following compounds in order of increasing acidity. (a) Benzoic acid, p-methylbenzoic acid, p-chlorobenzoic acid (b) p-Nitrobenzoic acid, acetic acid, benzoic acid Explain in each case your choice for the highest acidity.arrow_forward
- Define the Mechanism - Conversion of Carboxylic Acids to Amides with DCCarrow_forwardSuppose you were given the structural formula of compound B but only the molecular formulas for compound A and the starting bicyclic amine. Given this information, is it possible, working backward, to arrive at an unambiguous structural formula for compound A? for the bicyclic amine?arrow_forwardDuring a recent synthesis of hispidospermidin, a fungal isolate and an inhibitor of phospholipase C, the investigators employed employed a novel Friedel-Crafts acylation on a nonaromatic system (J. Am. Chem. Soc. 1998, 120, 4039-4040). The following acid chloride was treated with a Lewis acid, affording a mixture of two products, 1 and 2. Propose a plausible mechanism for the formation of compounds 1 and 2. CI AICI 进一步农 COCI 2 Part 1 Incorrect. Which of the four mechanistic steps is happening? Add curved arrow(s) to draw the first step of the mechanism. Modify the given drawing of the products as needed to show the intermediate that is formed in this step. Use the +/- tools to add/remove charges. CH₂ H St Edit Drawing H₂C H CH₂ CI Q M ΟΣarrow_forward
- Show how you might utilize the reduction of an amide, oxime, or a nitrile to carry out each of the following transformations (a)Benzoic acid to N-ethyl-N-benzylamine (b)1-Bromopentane to hexylamine (c)Propanoic acid to tripropylamine (d)2-Butanone to sec-butylaminearrow_forwardThe hydrocarbon fluorene was treated with potassium t-butoxide in an acid-base reaction, giving the fluorenide anion and t-butyl alcohol. (a) Which way does the equilibrium lie, and by how much? b) What is the proportion of the fluorenide anion to fluorene? (c) Why is fluorene so highly acidic, considering the pKa of an average alkane is above 50?arrow_forwardWrite the reactions involved in the following:(i) Hell-Volhard Zelinsky reaction(ii) Decarboxylation reactionarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning