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chemistry
organic chemistry
Questions and Answers of
Organic Chemistry
Propose a structure consistent with the following spectral data for a compound C8H18O2: IR: 3350 cm–1. 1H NMR: 1.24 δ (12 H, singlet); 1.56 δ (4 H, singlet); 1.95 δ (2 H, singlet)
The 1H NMR spectrum shown is that of 3-methyl-3-buten-l-ol. Assign all the observed resonance peaks to specific protons, and account for the splittingpatterns.
Compound A, C5H10O, is one of the basic building blocks of nature. All steroids and many other naturally occurring compounds are built from compound A. Spectroscopic analysis of A yields the
A compound of unknown structure gave the following spectroscopic data: Mass spectrum: M+ = 88.1. IR: 3600 cm–11H NMR: 1.4 δ (2 H, quartet, J = 7 Hz); 1.2 δ (6 H, singlet); 1.0 δ (1 H, singlet);
The following 1H NMR spectrum is that of an alcohol, C8H10O. Propose a structure.
Propose structures for alcohols that have the following 1H NMR spectra: (a) C5H12O (b) C8H10O
Propose structures for alcohols that have the following 1H NMR spectra: (a) C9H12O (b)C8H10O2
Compound A, C8H10O, has the IR and 1H NMR spectra shown. Propose a structure consistent with the observed spectra, and assign each peak in the NMR spectrum. Note that the absorption at 5.5 ?
Propose a structure for a compound C15H24O that has the following 1H NMR spectrum. The peak marked by an asterisk disappears when D2O is added to thesample.
The reduction of carbonyl compounds by reaction with hydride reagents (H: ?) and the Grignard addition by reaction with organo magnesium halides (R: ? + MgBr) are examples of nucleophilic carbonyl
Ethers can be prepared by reaction of an alkoxide or phenoxide ion with a primary alkyl halide. Anisole, for instance, results from reaction of sodium phenoxide with iodomethane. What kind of
Identify the functional groups in each of the following molecules: (a) Methionine, an amino acid: (b) Ibuprofen, a pain reliever: (c) Capsaicin, the pungent substance in chilipeppers:
Propose structures for simple molecules that contain the following functional groups:(a) Alcohol(b) Aromatic ring(c) Carboxylic acid(d) Amine(e) Both ketone and amine(f) Two double bonds
Identify the functional groups in the following model of arecoline, a veterinary drug used to control worms in animals. Convert the drawing into a line-bond structure and a molecular formula (red =
Draw structures of the five isomers of C6H14.
Propose structures that meet the following descriptions:(a) Two isomeric esters with the formula C5H10O2(b) Two isomeric nitriles with the formula C4H7N(c) Two isomeric disulfides with the formula
How many isomers are there with the following descriptions?(a) Alcohols with the formula C3H8O(b) Bromoalkanes with the formula C4H9Br
Draw the eight 5-carbon alkyl groups (pentyl isomers).
Identify the carbon atoms in the following molecules as primary, secondary, tertiary, orquaternary:
Identify the hydrogen atoms on the compounds shown in Problem 3.8 as primary, secondary, or tertiary.
Draw structures of alkanes that meet the following descriptions:(a) An alkane with two tertiary carbons(b) An alkane that contains an isopropyl group(c) An alkane that has one quaternary and one
Give IUPAC names for the followingcompounds:
Draw structures corresponding to the following IUPAC names:(a) 3, 4-Dimethylnonane(b) 3-Ethyl-4, 4-dimethylheptane(c) 2, 2-Dimethyl-4-propylocatane(d) 2, 2, 4-Trimethylpentane
Name the eight 5-carbon alkyl groups you drew in Problem 3.7.
Give the IUPAC name for the following hydrocarbon, and convert the drawing into a skeletal structure.
Make a graph of potential energy versus angle of bond rotation for propane, and assign values to the energy maxima.
Consider 2-methylpropane (isobutene). Sighting along the C2-C1 bond:(a) Draw a Newman projection of the most stable conformation.(b) Draw a Newman projection of the least stable conformation.(c) Make
Sight along the C2-C3 bond of 2, 3-dimethylbutane, and draw a Newman projection of the most stable conformation.
Draw a Newman projection along the C2-C3 bond of the following conformation of 2, 3-dimethylbutane, and calculate total strainenergy:
Identify the functional groups in the following substances, and convert each drawing into a molecular formula (red = O, blue =N):
Give IUPAC names for the following alkanes, and convert each drawing into a skeletal structure:
Locate and identify the functional groups in the following molecules. In these representations, each intersection of lines and the end of each line represents a carbon atom with the appropriate
Draw structures that meet the following description (there are many possibilities):(a) Three isomers with the formula C8H18(b) Three isomers with the formula C4H8O2
Draw structures of the nine isomers of C7H16.
In each of the following sets, which structures represent the same compounds and which represent different compounds?
There are seven constitutional isomers with the formula C4H10O. Draw as many as you can.
Propose structures that meet the following descriptions:(a) A ketone with five carbons(b) A four-carbon amide(c) A five-carbon ester(d) An aromatic aldehydes(e) A keto ester(f) An amino alcohol
Propose structures for the following:(a) A ketone, C4H8O(b) A nitrile, C5H9N(c) A dialdehyde, C4H6O2(d) A bromoalkene, C6H11Br(e) An alkane, C6H14(f) A cyclic saturated hydrocarbon, C6H12(g) A diene
Draw as many compounds as you can that fit the following descriptions:(a) Alcohols with formula C4H10O(b) Amines with formula C5H13N(c) Ketones with formula C5H10O(d) Aldehydes with formula C5H10O(e)
Draw compounds that contain the following:(a) A primary alcohol(b) A tertiary nitrile(c) A secondary Thiol(d) Both primary and secondary alcohols(e) An isopropyl(f) A quaternary carbon
Draw and name all monobromo derivatives of pentane, C5H11Br.
Draw and name all monochloro derivatives of 2, 5-dimethylhexane, C8H17C1.
Predict the hybridization of the carbon atom in each of the following functional groups:(a) Ketone(b) Nitrile(c) Carboxylic acid
Draw the structures of the following molecules:(a) Biacetyl, C4H6O2, a substance with the aroma of butter; it contains no rings or carbon—carbon multiple bonds.(b) Ethylenimine, C2H5N, a substance
Draw structures for the following:(a) 2-Methyiheptane(b) 4-Ethyl-2, 2-dimethylhexane(c) 4-Ethyl-3, 4-dimethyloctane(d) 2, 4, 4-Trimethylheptane(e) 3, 3-Diethyl-2, 5-dimethylnonane(f)
Draw a compound that:(a) Has only primary and tertiary carbons(b) Has no secondary or tertiary carbons(c) Has four secondary carbons
Draw a compound that:(a) Has nine primary hydrogens(b) Has only primary hydrogens
For each of the following compounds, draw an isomer that has the same functional groups. Each intersection of lines represents a carbon atom with the appropriate number of hydrogensattached.
Give IUPAC names for the followingcompounds:
Name the five isomers of C6H14. Discuss.
Explain why each of the following names is incorrect:(a) 2, 2-Dirnethyl-6-ethytheptane(b) 4-Ethyl-5, 5-dirnethylpentane(c) 3.Ethyl-4, 4-dimcthylhexane(d) 5, 5, 6-Trimcthyloctane(e)
Propose structures and give IUPAC names for the following:(a) A diethyldimethyihexane(b) A (3-methylbutyl)-substituted alkane
Consider 2-methylbutane (isopentane) Sighting along the C2—C3 bond:(a) Draw a Newman projection of the most stable conformation.(b) Draw a Newman projection of the least stable conformation.(c)
What are the relative energies of the three possible staggered conformations around the C2—C3 bond in 2, 3-dimethylbutane? (See Problem 3.42)
Construct a qualitative potential-energy diagram for rotation about the C—C bond of 1, 2-dibromoethane. Which conformation would you expect to be more stable? Label the anti and gauche
Which conformation of 1, 2-dibrornoethane (Problem 3.44) would you expect to have the larger dipole moment? The observed dipole moment of 1, 2-dibromoethane is μ = 1.0 D. What does this tell you
The barrier to rotation about the C—C bond in bromoethane is 15kJ/mol (3.6kcal/mol).(a) What energy value can you assign to an H—Br eclipsing interaction?(b) Construct a quantitative diagram of
Draw the most stable conformation of pentane, using wedges and dashes to represent bonds corning out of the paper and going behind the paper, respectively.
Draw the most stable conformation of 1, 4-dichiorobutane, using wedges and dashes to represent bonds coming out of the paper and going behind the paper, respectively.
Malic acid, C4H6O5, has been isolated from apples. Because this compound reacts with 2 molar equivalents of base, it is a dicarboxylic acid.(a) Draw at least five possible structures.(b) If malic
Formaldehyde, H2C = O, is known to all biologists because of its usefulness as a tissue preservative. When pure, formaldehyde trimerizes to give trioxane, C3H6O3, which, surprisingly enough, has no
Increased substitution around a bond leads to increased strain. Take the four substituted butanes listed below, for example. For each compound, sight along the C2-C3 bond and draw Newman projections
The cholesterol-lowering agents called statins, such as simvastatin (Zocor) and pravastatin (Pravachol), are among the most widely prescribed drugs in the world. Identify the functional groups in
We?ll look at cycloalkanes?saturated cyclic hydrocarbons? and we?ll see that the molecules generally adopt puckered, non-planar conformations. Cyclohexanc, for instance, has a puckered shape like a
We?ll see that there are two isomeric substances both named 1, 2-dimethylcyclohexane. Explain.
Give IUPAC names for the following cycloalkanes:
Draw structures corresponding to the following IUPAC names:(a) 1, 1-Dimethylcycloocatne(b) 2-Cyclobutylhexane(c) 1, 2-Dichlorocyclopentane(d) 1, 3-Dibromo-5-methylcyclohexane
Name the following cycloalkanes:
Name the following substances, including the cis- or trans-prefix:
Draw the structures of the following molecules:(a) Trans-1-Bromo-3-methylcyclohexane(b) Cis-1, 2-Dirnethylcyclobutane(c) Trails-1-tert-Butyl-2-ethylcyclohexane
Prostaglandin F2?, a hormone that causes uterine contraction during childbirth, has the following structure. Are the two hydroxyl groups (?OH) on the cyclopentane ring cis or trans to each other?
Names the following substances, including the cis-or trans-prefix (red-brown =Br):
Each H ↔ H eclipsing interaction in ethane costs about 4.0kJ/mol. How many such interactions are present in cyclopropane? What fraction of the overall 115 kJ/mol (27.5kcal/mol) strain energy of
Cis-l, 2-Dimethylcyclopropane has more strain than trans-1, 2-dimethylcyclo- propane. How can you account for this difference? Which of the two compounds is more stable?
How many H ↔ H eclipsing interactions would be present if cyclopentane were planar? Assuming an energy cost of 4.0kJ/mol for each eclipsing interaction, how much torsional strain would planar
Two conformations of cis-1, 3-dimethylcyclobutanc is shown. What is the difference between them, and which do you think is likely to be more stable?
Draw two different chair conformations of cyclohexanol (hydroxycyclohexane), showing all hydrogen atoms. Identify each position as axial or equatorial.
Draw two different chair conformations of trans-1, 4-dimethylcyclohexane, and label all positions as axial or equatorial.
Identify each of the colored positions?red, blue, and green?as axial or equatorial. Then carry out a ring-flip, and show the new positions occupied by each color,
What is the energy difference between the axial and equatorial conformations of cyclohexanol (hydroxycyclohexane)?
Why do you suppose an axial cyano (—CN) substituent causes practically no 1, 3-diaxial steric strain (0.4 kJ/mol)? Use molecular models to help with your answer.
Look at Figure, and estimate the percentages of axial and equatorial conformers present at equilibrium inbromo-cyclohexane.
Draw the most stable chair conformation of the following molecules, and estimate the amount of strain in each:(a) trans-1-Chloro-3-methylcyclohexane(b) cis-1-Ethyl-2-rnethylcyclohexane(c)
Identify each substituent in the following compound as axial or equatorial, and tell whether the conformation shown is the more stable or less stable chair form (yellow green ? CI):
Which isomer is more stable, cis-decalin or trans-decalin? Explain.
Name the following cycloalkanes:
Name the following compound, identify each substituent as axial or equatorial, and tell whether the conformation shown is the more stable or less stable chair form (yellow-greenC1):
A trisubstituted cyclohexane with three substituents? red, yellow, and blue?undergoes a ring-flip to its alternative chair conformation. Identify each substituent as axial or equatorial, and show the
Glucose exists in two forms having a 36 : 64 ratio at equilibrium. Draw a skeletal structure of each, describe the difference between them, and tell which of the two you think is more stable (red =
Draw the five cycloalkanes with the formula C5H10.
Draw two constitutional isomers of cis-1, 2-dibromo-cyclopentane.
Draw a stereoisomer of trans-1, 3-climethylcyclobutane.
Hydrocortisone, a naturally occurring hormone produced in the adrenal glands, is often used to treat inflammation, severe allergies, and numerous other conditions. Is the indicated ?OH group in the
A1, 2-cis disubstituted cyclohexane, such as cis-1, 2-dichlorocyclohexane, must have one group axial and one group equatorial. Explain.
A 1, 2-trans disubstituted cyclohexane must have either both groups axial or both groups equatorial. Explain.
Why is a 1, 3-cis disubstituted cyclohexane more stable than its transisomer?
Which is more stable, a 1, 4-trans disubstituted cyclohexane or its cis isomer?
Cis-l, 2-Dimnethylcyclohutane is less stable than its transisomer, hut cis-1, 3- dimethylcyclobutanc is more stable than its transisomer. Draw the most stable conformations of both, and explain.
Draw the two chair conformations of cis-1-chloro-2-methylcyclohexane. Which is more stable, and by how much?
Draw the two chair conformations of trans-1-chloro-2-mcthylcyclohexane. Which is more stable?
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