Concept explainers
Interpretation:
The structures of the compounds A, B, and C are to be predicted.
Concept Introduction:
▸ Electrophiles are electron deficient species which has positive or partially positive charge. Lewis acids are electrophiles which accept electron pair.
▸ Nucleophiles are electron rich species which has negative or partially negative charge. Lewis bases are nucleophiles which donate electron pair.
▸ Free radical is an atom, molecule or ion that has unpaired electrons which makes it highly chemically reactive.
▸ Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.
▸ Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.
▸ Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.
▸ The reaction in which hydrogen is added to the compound in the presence of catalyst is known as hydrogenation.
▸ The number of moles of hydrogen absorbed will be equal to the number of double bonds.
▸ Hydrogenation of
▸ Infrared spectroscopy is a simple, instrumental technique, which helps to determine the presence of various functional groups.
▸ It depends on the interactions of atoms or molecules with the
▸ The molecules which have dipole moment are IR active and the molecules which do not have dipole moment are IR inactive.
▸ The change in number of pairs of hydrogen atoms of a given compound and the acyclic compound which has the number of carbon atoms same as the number of carbon atoms in the given compound, is known as the Index of hydrogen deficiency.
▸ The Index of hydrogen deficiency can be denoted by IHD.
▸ The Index of hydrogen deficiency can be calculated by using the formula given below:
Here, C represents the number of carbon atoms, H represents the number of hydrogen atoms, N represents the number of nitrogen atoms and X represents the number of halogen atoms.
▸ The molecules which are non-superimposable or not identical with their mirror images are known as chiral molecules.
▸ A pair of two mirror images which are non-identical is known as enantiomers which are optically active.
▸ The objects or molecules which are superimposable with their mirror images are achiral objects or molecules and these objects have a centre of symmetry or plane of symmetry.
▸ The achiral compounds in which plane of symmetry is present internally and consists of chiral centres are known as meso compounds but they are optically inactive.
▸ The stereoisomers which are non-superimposable on each other and not mirror images of each other are known as diastereomers.
▸ Chiral molecules are capable of rotating plane polarized light
▸ The molecules which are superimposable or identical with their mirror images are known as achiral molecules, and achiral molecules are not capable of rotating the plane-polarised light.
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Chapter 7 Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
- Compound A, CH10, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a Pd/C catalyst. On treatment of A with dilute H,SO, dehydration occurred and an optically inactive alkene B, CH4 was produced as the major product. Alkene B, on ozonolysis, gave two products. Product C, C,H,0, was shown to be an aldehyde while product D, CHg0, was shown to be a ketone. Draw the structure of compound C. • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. In cases where there is more than one answer, jtust draw one.arrow_forwardA compound, C2H2O4, reacts with excess diazomethane to produce C4H,O4. Draw the structure of each compound. CH,N2 (excess) C2H2O4 C4H,O4arrow_forwardOzonolysis (O3 in CH2Cl2) of compound A under reducing conditions (Zn /acetic acid) gives formaldehyde, 2-butanone, and compound B. Catalytic hydrogenation (H2/Pd) of A gives 2,7-dimethylnonane. What is a possible structure for compound A? a. 2,7-Dimethyl-2,8-nonadieneb. 2,7-Dimethyl-1,8-nonadienec. 2,7-Dimethyl-1,6-nonadiened. 2,7-Dimethyl-1,7-nonadienearrow_forward
- Compound X has the molecular formula C7H14. Hydrogenation of compound X produces 2,4-dimethylpentane. Hydroboration-oxidation of compound X produces a racemic mixture of 2,4-dimethyl-1-pentanol. Predict the major product(s) obtained when compound X is treated with aqueous acid (H3O*). Draw all the substrates, reagents, and productsarrow_forwardDraw the structure of each product from the reaction of benzene with 2-chloro-1-methylcyclohexane using AlCl 3 as the catalyst and Identify the major product.arrow_forwardCr(VI) compounds are common reagents for the oxidation of alcohols. Primary alcohols are oxidized to carboxylic acids and secondary alcohols are oxidized to ketones. The mechanism involves a reaction similar to the E2 elimination, whereby a C=O double bond is formed with a reduced Cr(IV) compound as the leaving group.Draw curved arrows to show the movement of electrons in this step of the mechanism.arrow_forward
- Reaction of (CH3)3CH with Cl2 forms two products: (CH3)2CHCH2Cl (63%) and (CH3)3CCl (37%). Why is the major product formed by cleavage of the stronger 1° C–H bond?arrow_forwardCompound A (C6H12O2) reacts with water, acid, and heatto yield compound B (C5H10O2) and compound C (CH4O).Compound B is acidic. Deduce possible structures of compounds A, B, and Carrow_forwardHydrocarbon X has the formula C6H12.X reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form a product having 12 primary hydrogens.Treatment of X with ozone followed by zinc in aqueous acid gives a mixture two aldehydes.What is the structure of X?arrow_forward
- An unknown hydrocarbon A with the formula C6H10 reacts with 1 molar equivalent of H2 over a palladium catalyst to give B C6H12 (Rxn 1). Hydrocarbon A also reacts with OsO4 to give the glycol C (Rxn 2). A gives 5-oxohexanal on ozonolysis (Rxn 3). Draw the structures of A, B, and C. Give the reactions.arrow_forward5. Compound A, C 10H 18O, undergoes reaction with dilute H 2SO 4 at 50 °C to yield a mixture of two alkenes, C 10H 16. The major alkene B, gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Which of the following reactions are correct.arrow_forwardCompound A and compound B both have molecular formula C6H12. Both compounds produce epoxides when treated with a peroxy acid (RCO3H). The epoxide resulting from compound A was treated with aqueous acid (H3O+) and the resulting diol has no chiral centers. Identify the two possible structures for compound A (enter two numbers separated by commas with no spaces, e.g. "1,2") The epoxide resulting from compound B was treated with (H3O*) and the resulting diol was a meso compound. Identify compound B 2 3 potn 7 1 5 6 4 8arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning