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organic chemistry

Organic Chemistry 1st edition David R. Klein - Solutions

Identify the reagents you would use to accomplish each of the following transformations:a.b.c.d. CI CI ОН Но.
When butane reacts with Br2 in the presence of Cl2, both brominated and chlorinated products are obtained. Under such conditions, the usual selectivity of bromination is not observed. In other words, the ratio of 2-bromobutane to 1-bromobutane is very similar to the ratio of 2 chlorobutane to
Identify what reagents you would use to achieve each transformation:a. Conversion of 2-methyl-2-butene into a secondary alkyl halideb. Conversion of 2-methyl-2-butene into a tertiary alkyl halidec. Conversion of cis-2-butene into a meso diold. Conversion of cis-2-butene into enantiomeric diols
Identify the configuration of the chirality centers shown below:a.b.c.d. ОН Н -NH2 CH-Он ČH н Но- -н CHз
What reaction will take place if H2O is added to a mixture of NaNH2/NH3?
Draw a bond-line structure for each of the following compounds:a. CH2 = CHCH2C(CH3)3 b. (CH3CH2)2CHCH2CH2OHc. CH ≡ COCH2CH(CH3)2 d. CH3CH2OCH2CH2OCH2CH3e. (CH3CH2)3CBr f. (CH3)2C = CHCH3
Consider the following two compounds. Monochlorination of one of these compounds produces twice as many stereoisomeric products as the other. Draw the products in each case, and identify which compound yields more products upon chlorination.
Identify the reagents that you would use to accomplish each of the following transformations:a.b.c.d.e.f.g.h. Br-
What reaction will take place if H2O is added to a mixture of NaNH2/NH3?
Consider each pair of compounds below, and determine whether the pair represent the same compound, constitutional isomers, or different compounds that are not isomeric at all:a.b.c.d.
Compound A has molecular formula C5H10. Hydroboration-oxidation of compound A produces a pair of enantiomers, compounds B and C. When treated with HBr, compound A is converted into compound D, which is a tertiary alkyl bromide. When treated with O3 followed by DMS, compound A is converted into
Trans-1,3-Dichlorocyclobutane has a measurable dipole moment. Explain why the individual dipole moments of the C-Cl bonds do not cancel each other to produce a zero net dipole moment. CI- trans-1,3-Dichlorocyclobutane
In each reaction, identify the Lewis acid and the Lewis base:(a)(b)(c) Н ОН Н ОН он ӨF L-Ф
Determine the relationship between the two structures below. Are they resonance structures or are they constitutional isomers?
There are two different compounds with molecular formula C2H6O. One of these isomers has a much higher boiling point than the other. Explain why.
Propose an efficient synthesis for each of the following transformations. You might find it useful to review Section 11.13 before doing these problems.In section 11.13Radical halogenation provides a method for introducing functionality into an alkane.When the starting compound has only one kind of
How many stereo-isomers do you expect for the following compound? Draw all of the stereo isomers. ОН но, ОН
Draw the conjugate acid for each of the following bases:(a)(b)(c) NaNH2(d) H2O(e)(f)(g)(i) NaOH Ф
Below is the structure of caffeine, but its lone pairs are not shown. Identify the location of all lone pairs in this compound: н н с-н Н Н -N С—н Н N. П .C. нГн Caffeine Z-O-エ Z-U
Draw a Lewis structure of a carbon atom that is missing one valence electron (and therefore bears a positive charge). Which second-row element does this carbon atom resemble in terms of the number of valence electrons?
Using acetylene and 2-methylpropane as your only sources of carbon atoms, propose a plausible synthesis for 4-methyl-2-pentanone. You will need to utilize many reactions from previous chapters.
Determine whether syn dihydroxylation of trans-2-butene will yield the same products as anti dihydroxylation of cis-2-butene. Draw the products in each case and compare them.
The specific rotation of (S)-carvone (at 20°C) is +61. A chemist prepared a mixture of (R)-carvone and its enantiomer, and this mixture had an observed rotation of -55°.(a) What is the specific rotation of (R)-carvone at 20°C?(b) Calculate the % ee of this mixture.(c) What percentage of the
Identify the reagents you would use to achieve each of the following transformations: (a)(b)(c)(d)(e) OTs Он `CN он
Propylene is produced by cracking petroleum and is a very useful precursor in the production of many useful polymers. Propylene has one constitutional isomer. Draw that isomer, and identify its systematic name. Propylene
How many constitutional isomers are obtained when each of the following compounds undergoes monochlorination?(a)(b)(c)(d)(e)(f)(g)(h)(i)(j)
Syn dihydroxylation of the compound below yields two products. Draw both products and describe their stereo-isomeric relationship (i.e., are they enantiomers or diastereomers?): КMпO,, NaOH Cold
There are only two stereo-isomers of 1, 4-dimethylcyclohexane. Draw them, and explain why only two stereo-isomers are observed.
The rate at which two methyl radicals couple to form ethane is significantly faster than the rate at which two tert-butyl radicals couple. Offer two explanations for this observation.
Predict the products of each of the following reactions:a.b.c.d.e.f.g.h.i. 1) BH3 THF 2) H2O2, NaOH На Pt
Nicotine is an addictive substance found in tobacco. Identify the hybridization state and geometry of each of the nitrogen atoms in nicotine: Н н н Н C-H Н N. Н C- н H. Н Н Nicotine z: I I-O
Name one element that you would expect to exhibit bonding properties similar to boron. Explain?
Consider the structure of the following compound:(a) When this compound is treated with bromine under conditions that favor monobromination, two stereoisomeric products are obtained. Draw them, and identify whether they are enantiomers or diastereomers.(b) When this compound is treated with bromine
The following reaction is very slow:(a) Identify the mechanism.(b) Explain why the reaction is so slow.(c) When hydroxide is used instead of water, the reaction is very rapid. Draw the mechanism of this reaction, and explain why it is so fast. H20 HBг ОН Br
Below is the numbered skeleton of trans-decalin:Identify whether each of the following substituents would be in an equatorial position or an axial position:(a) A group at the C-2 position, pointing UP(b) A group at the C-3 position, pointing DOWN(c) A group at the C-4 position, pointing DOWN(d) A
Identify the most electronegative element in each of the following compounds:a) CH3OCH2CH2NH2b) CH2ClCH2Fc) CH3Li
When 2-methylpropane is treated with bromine in the presence of UV light, one product predominates.(a) Identify the structure of the product.(b) Draw the structure of the expected minor product.(c) Draw a mechanism for formation of the major product.(d) Draw a mechanism for formation of the minor
Identify the structure of the starting alkene in each of the following cases:a.b.c. 1) O3 C3H14 2) DMS C10H16 1) 03 2) DMS
Draw all possible stereo-isomers for each of the following compounds. Each possible Stereo-isomer should be drawn only once:a.b.c.d.e. но ОН
Draw the products obtained when 3,3,6-trimethylcyclohexene is treated with NBS and irradiated with UV light.
Predict the products that are expected when each of the following alkenes is treated with ozone followed by DMS:a.b.c.d.e.f.
Compare the Lewis dot structure of nitrogen and phosphorus and explain why you might expect these two atoms to exhibit similar bonding properties?
Compound A has molecular formula C5H12, and monobromination of compound A produces only compound B. When compound B is treated with a strong base, a mixture is obtained containing compound C and compound D. Using this information, answer the following questions:(a) Draw the structure of compound
Each of the following molecules has one plane of symmetry. Find the plane of symmetry in each case:a.b.c.d.e.f. CI Me Me Br
Myo-Inositol is a polyol (a compound containing many OH groups) that serves as the structural basis for a number of secondary messengers in eukaryotic cells. Draw the more stable chair conformation of myo-inositol. Он НО, ОН НО Он ОН
Draw the propagation steps that achieve the autooxidation of diethyl ether to form a hydroperoxide: OOH A hydroperoxide Diethyl ether
Predict the product(s) for each of the following reactions. In each case, make sure to consider the number of chirality centers being formed.a.b.c.d.e.f. Os0, (catalytic) NMO 1) OsO, 2) NaHSO, / H,O
The following compound is known to be chiral. Draw its enantiomer, and explain the source of chirality. CHз Нас Н
AmbienTMis a sedative used in the treatment of insomnia. It was discovered in 1982 and brought to market in 1992 (it takes a long time for new drugs to undergo the extensive testing required to receive approval from the Food and Drug Administration). Identify the hybridization state and geometry of
Identify all products expected for each of the following reactions. Take stereochemistry into account, and draw expected stereoisomer(s), if any:(a)(b)(c)(d) NBS hv
Compound A and compound B both have molecular formula C6H12. Both compounds produce epoxides when treated with MCPBA.a. The epoxide resulting from compound A was treated with aqueous acid (H3O+) and the resulting diol had no chirality centers. Propose two possible structures for compound A.b. The
Predict the major product(s) obtained upon bromination of (S)-3-methylhexane.
Under acid-catalyzed conditions, epoxides can be opened by a variety of nucleophiles other than water, such as alcohols. In such a case, the nucleophile will generally attack at the more substituted position. Using this information, predict the products for each of the following reactions:a.b. 1)
Consider the following two conformations of 2,3-dimethylbutane. For each of these conformations, use the following table to determine the total energy cost associated with all torsional strain and steric strain.(a)(b) ENERGY COSTS FOR COMPARING THE RELATIVE ENERGY OF CONFORMATIONS ENERGY COST (K./
Chlorination of (S)-2-chloropentane produces a mixture of isomers with molecular formula C5H10Cl2. How many isomers are obtained (consider stereoisomers as separate products)? Draw all of the products.
Identify all transition states and intermediates on the following energy diagram: Free energy (G) Reaction coordinate
Identify the major product(s) for each of the following reactions. If any of the reactions do not yield a product, indicate €œno reaction.€(a)(b)(c)(d)(e)(f) Br2 hv I2 I2 hv
Rank the following conformations in order of increasing energy: Br Br Br Br На H- н Н н Н нн Br н Br Br Н- На Н Н НН Br
Sketch an energy diagram showing the conformational analysis of 2,2,3,3-tetramethylbutane. Use the following table to determine the energy difference between staggered and eclipsed conformations of this compound. ENERGY COSTS FOR COMPARING THE RELATIVE ENERGY OF CONFORMATIONS ENERGY COST (K./ MOL)
Abstraction of a hydrogen atom from 3-ethylpentane can yield three different radicals, depending on which hydrogen atom is abstracted. Draw all three radicals and rank them in order of increasing stability.
One object below has three planes of symmetry. Identify that object.a.b.c.d.e.f.
Glucose (a sugar) is produced by photosynthesis and is used by cells to store energy. Draw the most stable conformation of glucose: но Но, Но ОН он Glucose
For each of the products shown in the following reaction, propose a mechanism that explains its formation: Br NBS, hv Br
Predict the products that are expected when each of the following alkenes is treated with a peroxy acid (such as MCPBA) followed by aqueous acid:a.b.c.d.e.f.
The following reaction is very slow. Identify the mechanism, and explain why the reaction is so slow. Br NaOH, ОН
Draw a Newman projection of the following compound, as viewed from the angle indicated. CI Br CI Br
Draw the conjugate base for each of the following acids:(a)(b)(c) NH3(d) H3O+(e)(f)(g)(h) NH4+ Но.
For each of the following pairs of compounds, determine which compound is more stable (you may find it helpful to draw out the chair conformations):(a)(b)(c)(d) II
For each of the following cases, read the curved arrows and identify which arrow-pushing pattern is utilized:a.b.c.d.e.f.g.h.i. :Ci: -0-H нӧ- 0-H 0:0-I :O:
When trans-1-phenylpropene is treated with bromine, some syn addition is observed. Explain why the presence of a phenyl group causes a loss of stereospecificity. Br + En Br2 En Br Br Syn addition products (17%) trans-1-Phenylpropene Anti addition products (83%)
Identify the product of the following reaction: Br Br ONa 2 NaBr C4H3O2 Nao
Draw both chair conformations for each of the following compounds. In each case, identify the more stable chair conformation:(a) Methylcyclohexane(b) Trans-1,2-Diisopropylcyclohexane(c) Cis-1,3-Diisopropylcyclohexane(d) Trans-1,4-Diisopropylcyclohexane
Menthol, isolated from various mint oils, is used in the treatment of minor throat irritation. Draw both chair conformations of menthol, and indicate which conformation is lower in energy. ОН Menthol
The barrier to rotation of bromoethane is 15 kJ/mol. Based on this information, determine the energy cost associated with the eclipsing interaction between a bromine atom and a hydrogen atom.
Identify the compounds below that can function as Lewis bases: N'
Assign IUPAC names for each of the following compounds: (a)(b)(c)(d) H H- CH- 13
Assign IUPAC names for each of the following compounds:(a)(b)(c)(d) Н Н н н. CH н н На CH3 Н н н Н
Identify the product(s) in each of the following reactions:(a)(b)(c)(d) Br ETOH
Draw a relative energy diagram showing the conformational analysis of 1,2-dichloroethane. Clearly label all staggered conformations and all eclipsed conformations with the corresponding Newman projections.
Each of the following reactions proceeds via an SN1 mechanism and will have anywhere from two to five steps, as discussed in Section 7.6. Determine the number of steps for each reaction, and then draw the mechanism in each case:(a)(b)(c)(d) OMe CI Меон HCI CI SH NaSH Naci
For each of the following objects determine whether or not it possesses a plane of symmetry:a.b.c.d.e.f.
Bromonium ions can be captured by nucleophiles other than water. Predict the products of each of the following reactions:a.
Draw the mechanism of the following reaction: ONa + NaBr Br
Identify the relationship between the following two compounds. Он н ОН Н
Propose a mechanism for the following transformation: CI ОН HCI Нао
For each of the following cases use the information given to determine whether or not the equilibrium will favor products over reactants:(a) A reaction with Keq = 1.2(b) A reaction with Keq = 0.2(c) A reaction with a positive ΔG(d) An exothermic reaction with a positive ΔS(e) An endothermic
Draw the carbocation intermediate that would be formed if each of the following substrates would participate in an SN1 reaction. In each case, identify the carbocation as being primary, secondary, or tertiary.(a)(b)(c)(d) CI
In each case below, identify the Lewis acid and the Lewis base:(a)(b)
List the following carbocations in order of increasing stability:
Predict which of the following compounds is more acidic. After making your prediction, use the pKavalues from the following table to determine whether your prediction was correct. ACID pka CONJUGATE BASE Weakest Strongest acid for baso -0- -0- -7 -2.9 н "н -1.74 4.75 9.0 нн 9.9 н 15.7 Ay-00 16
(R)-2-Pentanol racemizes when placed in dilute sulfuric acid. Draw a mechanism that explains this stereochemical outcome, and draw an energy diagram of the process.
The specific rotation of L-dopa in water (at 15°C) is -39.5. A chemist prepared a mixture of L-dopa and its enantiomer, and this mixture had a specific rotation of -37. Calculate the % ee of this mixture.
We will learn all of the following reactions in upcoming chapters. For each of these reactions, notice that the product is an anion (ignore the positively charged ion in each case). In order to obtain a neutral product, this anion must be treated with a proton source in a process called
Identify the hybridization state and geometry of each carbon atom in the following compounds:a.b.c. Н н -OEJ- -CEC-C Н. .C. H. н1 H' н Н т.
For each case below, identify the most likely value for x:a) BHxb) CHx c) NHx d) CH2Clx
Which of the following pure compounds will exhibit hydrogen bonding?a) CH3CH2OH b) CH2O c) C2H4 d) C2H2e) CH3OCH3 f) CH3NH2g) C3H8 h) NH3
Triphenylmethane readily undergoes autooxidation to produce a hydroperoxide:(a) Draw the expected hydroperoxide.(b) Explain why triphenylmethane is so susceptible to autooxidation.(c) In the presence of phenol, triphenylmethane undergoes autooxidation at a much slower rate. Explain this
AIBN is an azo compound (a compound with a N=N double bond) that is often used as a radical initiator. Upon heating, AIBN liberates nitrogen gas to produce two identical radicals:(a) Give two reasons why these radicals are so stable.(b) Explain why the following azo compound is not useful as a
When ethylbenzene is treated with NBS and irradiated with UV light, two stereoisomeric compounds are obtained in equal amounts. Draw the products and explain why they are obtained in equal amounts. NBS hv two products
When the following optically active alcohol is treated with HBr, a racemic mixture of alkyl bromides is obtained:Draw the mechanism of the reaction, and explain the stereochemical outcome. Br Он HBr + H20 Racemic mixture Мн

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