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chemistry
organic chemistry

Questions and Answers of Organic Chemistry

Draw the two chair conformations for ethyl cyclohexane which is more stable.
Which of these compounds will have more of the conformation with the substituent on the cyclohexane ring axial present at equilibrium?
Bromine is larger than chlorine, yet the two atoms have identical axial destabilization energies. Explain.
Draw the stereo isomers of these compounds:(a) 1, 3-Dimethyleyclohexane(b) 1, 2-Diethylcycloproane(c) 1-Chloro-3-methylcyclopentane
Draw both chair conformations of trans-1, 3-dimethyl cyclohexane indicate whether each methyl group is axial or equatorial.
Consider the two stereo isomers of 1, 4-dimethyl cyclohexane:(a) Explain whether each methyl is axial or equatorial in the conformations of the cis-isomer.(b) Explain whether each methyl is axial or
Consider the two stereo isomers of 3-isoproplcyclohexanol.(a) Which is the more stable conformation of each stereo isomer?(b) Which is the more stable stereo isomer by how much?
For thee compounds indicated whether the substituents are cis or trans whether they are axial or equatorial, whether the conformation shown or the other chair conformation is more stable, and whether
Draw all the cis-trans isomers for these compounds:(a) CH3CH = CHCH = CHCH2CH3(b) CH3CH = CHCH = CHCH3(c) CH3CH = CHCH = CH2
Which of these groups has the higher priority?
Assign the configurations of these compounds as Z or E:
How would the energy versus dihedral angle plot for 2-methylpropane (isobutene) differs from that for propane?
Draw an energy versus dihedral angle plot for the conformations of 2, 3-dirnethylbutane about the C-2—C-3 bond.
Discuss the geometry and the types of strain present in these compounds:(a) Cyclopropane(b) Cyclobutene(c) Cyclopentane(d) Cyclohexane(e) Cyclodecane
Explain why the axial strain energies for the — C ≡ N group and the — C ≡ CH group are much smaller than that for the CH3 group.
Draw the chair conformations of 1, 1, 3—trimethyl cyclohexane. Which conformation is more stable? Why is it not possible on the basis of the material in this chapter to determine the exact energy
Draw the cis and trans stereo isomers of this compound and explain their relative stabilities.
Draw both chair conformations of 1-methyl-1-phenylcyclohexane. Which is more stable by how much energy?
Explain whether the methyl is axial or equatorial in this compound:
Draw both chair conformations for menthol (a component of peppermint oil) and its stereo isomer, neo menthol. Which groups are axial and which groups are equatorial? Explain which conformation is
Draw the structures of these compounds.(a) (E)-3-Hexene(b) (Z)-2-Chloro-3-isopropyl-2-heptene
Which of these compounds can form an intra molecular (within the same molecule) hydrogen bond between the hydrogen of the carboxylic acid and the oxygen of the ether group? Explain.
Draw Newman projections for the anti and gauche conformations about the C – C bond of these compounds. What other factors, besides steric and tor-sional strain, influence the stability of these
Explain which is more stable, cis-1, 2-dimethylcyclopropane or trans-1, 2-dimethylcyclopropane.
Linoleic acid and α-linolenic acid are two naturally occurring us-saturated fatty acids that are components of fats. Explain how many cis-trans isomers exist for each of these of these fatty acids.
Penicillin's are relatively unstable compounds and are usually stored in a refrigerator for this reason. Suggest a factor that contributes to the reactivity of penicillin G.
Build a handheld model of bicycle [2.2.1] heptanes and discuss the types of strain that are present in this compound.
Explain whether the compound shown is the Z or the E diastereomer. Problems using online Three-Dimensional molecular models
Explain whether the conformation shown is the most stable conformation of each of these molecules. Problems using online Three-Dimensional molecular models
Explain which stereo isomer is more stable. Problems using online Three-Dimensional molecular models
Explain which isomer has more strain energy in the conformation shown. Problems using online Three-Dimensional molecular models
For these compounds, indicate whether the substituent’s are cis or Trans, whether they are axial or equatorial, whether the conformation shown or the other chair conformation is more stable, and
Indicate whether each of these objects is chiral or achiral:(a) Golf ball(b) Baseball glove(c) Clock(d) T-shirt(e) Dress shirt(f) Automobile
Determine whether each of these molecules is chiral, for those that are chiral, put an asterisk at the chirality center.
Indicate whether each of these objects or molecules has a plane of symmetry:
Assign priorities to the groups attached to the chirality centers of these molecules and determine whether they have the R or S configuration:
Draw structures for these compounds:(a) (R)-3-Ethylcylohexene(b) (R)-2-Bromoheptane
Consider the two enantiomers of 2-pentanol. Explain whether each of these statements is true, is false, or cannot be determined from this information.(a) (R)-2-Pentanol is a stronger acid than
Draw all the stereo isomers of 2-bromo-3-chlorobutane and indicate whether they are enantiomers or diastereomers.
Label each chirality center in these compounds with an asterisk and calculate the maximum number of stereo isomers for each.
Draw all of the stereo isomers for 2, 3-dichlorobutane. Indicate which rotate plane-polarized light and which are meso.
Draw all of the stereo isomers of 1, 2-dimethylcyclopropane. Explain which rotate plane-polarized light.
Explain whether these compounds rotate plane-polarized light:
Draw Fischer projections for these compounds?
Assign the configurations of the compounds represented by these Fischer projections as R or S.
Explain whether each of these compounds is chiral or not:
Although this biphenyl is chiral, it cannot be resolved. Explain.
Assign the configuration of these compounds as R or S:
Draw the structures of these compounds:(a) (R)-3-Chloro-1-pentene(b) (S)-1-Methyl-2-cyclohexenol
Determine the number of stereo isomers for these compounds:
Draw all of the stereo isomers of these compounds:
Explain whether or not these compounds would rotate plane-polarized light:
Identify these pairs of compounds as identical, structural isomers, enantiomers, ordiastereomers:
Identify these pairs of compounds as identical, structural isomers, enantiomers, or diastereomers:
(a) A solution of 0.2g/mL of a compound in a 1 dm cell rotates plane-polarized light + 13.3o at the sodium D line. What is the specific rotation of this compound?(b) What is the rotation caused by a
Describe how this amine could be resolved by using this carboxylic acid?
An unknown compound, X has the formula C6H12.(a) Calculate the degree of un-saturation of X.(b) X reacts with H2 in the presence of a catalyst to form a compound, Y, with the formula C6H14. What
How many stereo isomers exist for this compound? Assign the relative stabilities of each. Is the methyl group axial or equatorial in the more stable conformer of the least stable stereo isomer?
Draw a stereo isomer of this compound that is chiral, and draw two that are not chiral?
All naturally occurring amino acids have the same relative configuration. All have the S absolute configuration, except for cysteine, which has the R configuration.Explain.
Explain whether each of these compounds is chiral or not:
Indicate whether these compounds are identical, enantiomers, or diastereomers.
Determine whether each of the compounds is the R or the S enantiomers.
Determine whether each of these compounds is chiral or not.
What is the relationship between the model and the Fischer projection?
How many chirality centers are present in estradiol how many stereo isomers does estradiol have?
Show the products, including stereo chemistry, of these SN2 reactions:
Explain which compound has a faster rate of SN2 reaction:
Arrange these compounds in order of decreasing SN2 reaction rate:
Draw a free energy versus reaction progress diagram for a reaction that occurs in two steps with a relatively stable intermediate and in which the transition state for the second step is the
Consider the free energy versus reaction progress diagram for the SN2 reaction shown in Figure 8.1. Does the transition state for this reaction have the C – Cl bond less than half broke,
Explain which compound has a faster rate of SN1 reaction.
Arrange these compounds in order of decreasing SN1 reaction rate.
Show the products, including stereo chemistry, of these SN1 reactions:
Explain whether this reaction would follow the SN1 or the SN2 mechanism and then explain which reaction is faster:
(a) Show all the steps in the mechanism for this reaction. Don't forget to use curved arrows to show the movement of electrons in each step of the mechanism. (b) Show a free energy versus reaction
Explain which of these reaction proceeds at a faster rate:
Show the products and the mechanisms of the following reactions. Don't forget to use curved arrows to show the movement of electrons in each step of the mechanism.
Show all of the steps in the mechanism for this reaction:
Explain why the carbocation shown in Figure 8.8 has a longer lifetime than it does under the conditions shown in Figure 9.8.
Explain in which solvent these reaction are faster:
Explain whether these reactions follow an SN1 or an SN2 mechanism.
Show the products of these reactions. (Remember that acid-base reactions are usually much faster than nucleophilic substitution reactions.)
Show both the substitution and elimination products that are formed in these reactions:
Show the rearranged carbocations that are expected from these carbocations:
Show the substitution products for these reactions:
(a) Show all of the steps in the mechanism for this reaction. Don't forget to use curved arrows to show the movement of electrons in each step of the mechanism. (b) Show a free energy versus reaction
Which of these compounds would have a faster rate of SN2 reaction?
Which of these compounds would have faster rate of SN1 reaction?
Arrange these compounds in order of increasing SN2 reaction rate:
Arrange these compounds in order of increasing SN1 reaction rate:
Show the products of these reactions and explain whether each would follow an SN1 or an SN2 mechanism:
Explain whether each pair of reaction should follow an SN1 or an SN2 mechanism. Then explain which member of the pair should proceed at a faster rate.
Show all of the steps in the mechanisms of these reactions:
This reaction gives three substitution products (not counting E/Z isomers). Show the structures of these products and show the mechanism for the irformation:
Explain why the trifluoromethanessulfonate anion is a better leaving group than the mesylate anion.
When benzyl tosylate is heated in methanol, the product is benzyl methyl ether. When bromide ion is added to the reaction, the reaction proceeds at exactly the same rate, but the product is now
The substitution of bromo methane with hydroxide ion proceeds about 5000 times faster than the reaction of bromomethane with water. However, the substitution reaction of 2-bromo-2-methylpropane
Explain why this primary halide reacts very rapidly under condition that is favorable for the SN1 mechanism: CH3 – O – CH2 – Cl
Ethers can be cleaved by treatment with strong acids. Show all of the steps in the mechanism for this reaction and explain why these products are formed rather than iodomethane and2-methyl-2-butanol:

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