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organic chemistry
Organic Chemistry 1st edition David R. Klein - Solutions
Draw a Lewis structure of a carbon atom that has one extra valence electron (and therefore bears a negative charge). Which second-row element does this carbon atom resemble in terms of the number of valence electrons?
When methyloxirane is treated with HBr, the bromide ion attacks the less substituted position. However, when phenyloxirane is treated with HBr, the bromide ion attacks the more substituted position.Explain the difference in regiochemistry in terms of a competition between steric effects and
Epoxides can be formed by treating α-haloketones with sodium borohydride. Propose a mechanism for formation of the following epoxide. NABH,
Predict the product of the following reaction. Mет н 1) LIAID, 2) H20 Me
Propose a structure for a compound with molecular formula C4H10O that exhibits the following1H NMR spectrum. Proton NMR 2 3.0 4.0 2.5 Chemical shift (ppm) 2.0 3.5 1.5 1.0
Propose a structure for a compound with molecular formula C4H8O that exhibits the following13C NMR and FTIR spectra. Carbon NMR 67.7- 25.4- 80 30 20 100 90 70 60 40 10 Chemical shift (ppm) 100 80 60- 40- 20- 0- 4000 3000 2000 1500 1000 2500 3500 Wavenumbers (cm-1) % Transmittance
Propose a structure for a compound with molecular formula C8H18O that exhibits the following1H NMR and13C NMR spectra. Proton NMR 3.0 2.0 Chemical shift (ppm) 4.0 3.5 2.5 1.5 1.0 0.5 Carbon NMR -70.5 31.6- 19.3- -13.7 70 60 50 40 30 20 10 Chemical shift (ppm) 3.
Propose a structure for ether with molecular formula C7H8O that exhibits the following13C NMR spectrum. Carbon NMR 114.0 129.5, 120,714.0 55.1- 159.71 160 120 140 100 100 Chemical shift (ppm) 80 80 60 60 40
Propose a plausible synthesis for each transformation.a.b.c.d.e.f.g.h.i.j.k.l.m.n.o.p.q.r.s.t.u. ОН
Fill in the missing products below. excess HI Heat 1) Hg(OAc), Etон 2) NABH, Н-СЕс: Na MCPBA 1) NaSH 2) H20 HBr
Fill in the missing reagents below. Me Он Он OEt ?| Br ОН ОН Me SH OEt OMe OEt ОН ОН CN
Using acetylene and ethylene oxide as your only sources of carbon atoms, propose a synthesis for each of the following compounds.a.b. Но ОН Н Н
Recall that a C=C bond is comprised of a s bond and a p bond. These two bonds together have a combined BDE (bond dissociation energy) of 632 kJ/mol. Use this information to predict whether the following reaction is exothermic or endothermic: н н Н-о но. Н Н
Atropine, extracted from the plant Atropa belladonna, has been used in the treatment of bradycardia (low heart rate) and cardiac arrest. Draw the enantiomer of atropine: CHз н 0= -Он
In each case, identify the more stable anion. Explain why it is more stable.(a)(b)(c) vs. N. vs. -zo
Determine the electron configuration for each of the following atoms:a. Carbon b. Oxygen c. Boron d. Fluorine e. Sodium f. Aluminum
Using any reagents you like, show a way to convert 1-methylcyclopentene into 3-methylcyclopentene.
Suggest suitable reagents to perform the following transformation: Он Racemic
Atorvastatin is sold under the trade name Lipitor and is used for lowering cholesterol. Annual global sales of this compound exceed $13 billion. Assign a configuration to each chirality center in atorvastatin: neee ОН Он N.
Consider the structures of cis-decalin and trans-decalin:(a) Which of these compounds would you expect to be more stable?(b) One of these two compounds is incapable of ring flipping. Identify it and explain your choice. Н cis-Decalin trans-Decalin
(R)-Limonene is found in many citrus fruits, including oranges and lemons:Draw the structures and identify the relationship of the two products obtained when (R)-limonene is treated with excess hydrogen in the presence of a catalyst.
Draw the enantiomer of each compound in the previous problem.a.b.c. Он Н н- -ОН но- —н H- -ОН ČH,OH Он но- -н Но- но- -н CH-OН I I I
Draw the enantiomer for each of the following compounds:a.b.c.d.e.f.g.h.i.j.k.l. CI.
Draw all significant resonance structures for each of the following compounds: ОН Он НО Testosterone Estradiol (Female sex hormone) (Male sex hormone)
Propose a plausible synthesis for each of the following transformations:a.b. Он ОН
Identify the reagents necessary to achieve each transformation below:(a)(b)(c) D D D
Suggest suitable reagents to perform each of the following transformations: Br- En Br ОН Но. En
Identify the number of stereoisomers expected for each of the following:a.b.c.d.e.f. CI Он ОН Он Он
If we compare the sizes of the halogens, we find that they increase in size from fluorine to iodine. Nevertheless, fluoroethane, chloroethane, bromoethane, and iodoethane all have very similar barriers to rotation about the C—C bond. Can you offer a possible
Write an equation for the proton transfer reaction that occurs when each of the following bases reacts with water. In each case, draw curved arrows that show the mechanism of the proton transfer:(a)(b)(c)(d) .
Using acetylene as your only source of carbon atoms, identify a synthetic route for the production of 1-bromobutane.
Compound A has molecular formula C7H15Br. Treatment of compound A with sodium ethoxide yields only one elimination product (compound B) and no substitution products. When compound B is treated with dilute sulfuric acid, compound C is obtained, which has molecular formula C7H16O. Draw the structures
Consider the following SN2 reaction:(a) Draw the mechanism of this reaction.(b) What is the rate equation of this reaction?(c) What would happen to the rate if the solvent is changed from DMSO to ethanol?(d) Draw an energy diagram of the reaction above.(e) Draw the transition state of this
Using acetylene as your only source of carbon atoms, identify a synthetic route for the production of 2-bromobutane.
Suggest an efficient synthesis for each of the following transformations:a.b. Он ОН
Determine the configuration for every chirality center in each of the following compounds.a.b.c. HO но H- но- OH ČH,OH
Identify the reagents necessary to achieve each of the following transformations: Br Br Br Br Br
Suggest an efficient synthesis for each of the following transformations:a.b.c.d. Br Br
Identify all of the nucleophilic centers in each of the following compounds:a.b.c.d. Li ОН NH2
For each of the following reactions predict the sign of ΔG. If a prediction is not possible because the sign of ΔG will be temperature dependent, describe how ΔG will be affected by raising the temperature.(a) An endothermic reaction for which the system exhibits an increase in entropy(b) An
Determine the configuration for every chirality center in each of the following compounds.a.b.c. но Н- -он но- -н Н- -ОН CH-он но Но Но Но -н CH-он IтI
Identify the reagents necessary to achieve each of the following transformations: Br но Br -Он "ОН Он Br Он Br "Br
Compound A is an alkene that was treated with ozone (followed by DMS) to yield only 4-heptanone. Identify the major product that is expected when compound A is treated with MCPBA followed by aqueous acid (H3O+).
Consider the three compounds shown below and then answer the questions that follow:a) Which two compounds are constitutional isomers?b) Which compound contains a nitrogen atom with trigonal pyramidal geometry?c) Identify the compound with the greatest number of σ bonds.d) Identify the
The regions of δ+ in a compound are the regions most likely to be attacked by an anion, such as hydroxide (HO-). In the compound below, identify the two carbon atoms that are most likely to be attacked by a hydroxide ion: H o H H H H-C-C-ċ-ċ-C-CI: H H H
Using acetylene as your only source of carbon atoms, design a synthesis of pen-tanal. (Pentanal has an odd number of carbon atoms, while acetylene has an even number of carbon atoms): H.
How many different alkenes will produce 2, 4-dimethylpentane upon hydrogenation? Draw them.
Identify the reagent you would use to accomplish each of the following transformations:(a) Cyclobutanol → bromocyclobutane(b) tert-Butanol → tert-butyl chloride(c) Ethyl chloride → ethanol
The following compound is optically inactive. Explain why.
Melatonin is an animal hormone believed to have a role in regulating the sleep cycle:The structure of melatonin incorporates two nitrogen atoms. What are the hybridization state and geometry of each nitrogen atom? Explain your answer. ОСНа N- LN. H' H-N Melatonin
Using acetylene as your only source of carbon atoms, design a synthesis of cis-3- decene:
The following four reactions will be the focus of the upcoming chapters (substitution and elimination reactions). Draw the curved arrows that accomplish each of the transformations shown:a.b.c.d. Br CI Br CI cP
Draw bond-line structures using wedges and dashes for the following compounds:a.b.c.d.e. CH, Н -ОН —н Но- Н- -ОН CH- Et Н- -ОН Но —н Н. -он ОН Me
Consider the structures of cis-1,2-dimethylcyclopropane and trans-1,2-dimethylcyclopropane:(a) Which compound would you expect to be more stable? Explain your choice.(b) Predict the difference in energy between these two compounds. A A
Using acetylene as your only source of carbon atoms, design a synthesis of trans-5- decene:
Below are two potential methods for preparing the same ether, but only one of them is successful. Identify the successful aproach and explain your choice. NaOMe ONa CH3I
The specific rotation of vitamin C (using the D line of sodium, at 20°C) is +24. Predict what the observed rotation would be for a solution containing 0.100 g of vitamin C dissolved in 10.0 mL of ethanol and placed in a sample cell with a length of 1.00 dm.
Cis-1,3-Dimethylcyclobutane has two planes of symmetry. Draw the compound and identify both planes of symmetry.
Propose a plausible synthesis for each of the following transformations:a.b.c.d.e.f.g. Br ОН Br
Suggest an efficient synthesis for each of the following transformations:a.b.
Write an equation for the proton transfer reaction that occurs when each of the following acids reacts with water. In each case, draw curved arrows that show the mechanism of the proton transfer:(a) HBr(b)(c)(d) Н-о—$—0—н Н
Methylene chloride (CH2Cl2) has fewer chlorine atoms than chloroform (CHCl3). Nevertheless, methylene chloride has a larger molecular dipole moment than chloroform. Explain.
Propose a plausible synthesis for the following transformation, in which the carbon skeleton is increased by only one carbon atom: H.
Compound A reacts with one equivalent of H2 in the presence of a catalyst to give methylcyclohexane. Compound A can be formed upon treatment of 1-bromo-1-methylcyclohexane with sodium methoxide. What is the structure of compound A?
For each of the following compounds, identify any polar covalent bonds by drawing δ+ and δ- symbols in the appropriate locations.a. b.c.d.e.f. нн н Н Н-с—ӧ—с—с-ӧ—с—н Н нн н :F: Н-с —сі: CI Н
Propose a plausible synthesis for the following transformation (many steps are required): Он Но
Draw a Lewis structure for each of the following ions; in each case, indicate which atom possesses the formal charge:a. BH4b. NH2c. C2H5+
Identify reagents that can be used to achieve each of the following transformations:a.b.c.d.e.f. Br Br HO,
Propose a mechanism for each of the following reactions:a.b.c.d. ОН Он н,о* Он Н,о*
What products would you expect from the reaction between (S)-2-iodobutane and each of the following nucleophiles?(a) NaSH (b) NaSEt (c) NaCN
Identify any formal charges in the compounds below:a. b.c.d.e.f.g.h.i. Н H-Al-H Н I-
When 3-bromo-3-ethylpentane is treated with sodium acetylide, the major products are 3-ethyl-2-pentene and acetylene. Explain why the carbon skeleton does not change in this case, and justify the formation of the observed products.
Predict the major product(s) for each of the following reactions: 1) MCPBA 1) ВН, THF 2)Н,О, NaOH 2) Н,о* ВГz НЕ. На Pt
Would water be a suitable proton source to protonate the following compound? ONa
There are four constitutional isomers with molecular formula C3H9N. Draw a Lewis structure for each isomer and determine the number of lone pairs on the nitrogen atom in each case?
Propose a plausible synthesis for each of the following transformations:a.b.c. Br Br Н
Borane (BH3) is very unstable and quite reactive. Draw a Lewis structure of borane and explain the source of the instability.
Identify reagents that can be used to achieve each of the following transformations:a.b.c. Br
Draw a Lewis structure for each of the following compounds:(a) C2H6 (b) C2H4 (c) C2H2(d) C3H8 (e) C3H6 (f) CH3OH
Predict the major product(s) for each of the following reactions: 1) Hg(OAC)2, Н-0 2) NABH, ? - КМпO, NaOH, cold Br2 НС H20 Pt
For each pair of compounds below, determine whether they are identical compounds, constitutional isomers, stereoisomers, or different conformations of the same compound:(a)(b)(c)(d)(e)(f)(g)(h)(i)(j)(k)(l) CH,CH3 -CНз CHз H3C. Н- CH-CHз CH2CH3 Н Н Н
Do you expect cyclohexene to adopt a chair conformation? Why or why not? Explain. Cyclohexene
Identify the reagents you would use to convert methylcyclohexane into each of the following:(a) A 3° alkyl halide(b) A trisubstituted alkene(c) A 2° alcohol(d) 3-methylcyclohexene
At high temperatures, alkanes can undergo dehydrogenation to produce alkenes. For example:This reaction is used industrially to prepare ethylene while simultaneously serving as a source of hydrogen gas. Explain why dehydrogenation only works at high temperatures. Н. нн 750 °C. Н
Identify the reagents you would use to convert 1-pentene into a geminal dibromide (“geminal” indicates that both bromine atoms are connected to the same carbon atom).
Would ethanol (CH3CH2OH) be a suitable solvent in which to perform the following proton transfer? Explain your answer: ONH2 + NH3 NH2 H.
Identify the reagents you would use to convert 2-bromo-2-methylbutane into 3-methyl-1-butyne.
Propose a plausible synthesis for each of the following transformations:a.b.c.d.e.f.g.h. Br Br
Identify the reagents you would use to accomplish each of the following transformations:a.b.
Identify the reagents you would use to accomplish each of the following transformations:a.b.
Identify the reagents necessary to accomplish each of the following transformations. If you are having trouble, the reagents for these transformations appear on page 482, but you should first try to identify the reagents yourself without help: Br Br- -Cн Br Br Br Br. Br Br Br Он
Identify the reagents you would use to accomplish the following transformation - Br Br
Each of the following compounds can be prepared with an alkyl iodide and a suitable nucleophile. In each case, identify the alkyl iodide and the nucleophile that you would use.(a)(b)(c)(d)(e)(f) он
Identify the reagents you would use to accomplish each of the following transformations:(a) Convert 2-methyl-2-butene into a monosubstituted alkene(b) Convert 2,3-dimethyl-1-hexene into a tetrasubstituted alkene
Identify the reagents necessary to accomplish each of the transformations shown below. If you are having trouble, the reagents for these transformations appear on page 444, but you should first try to identify the reagents yourself without help:
Identify the reagents you would use to achieve each of the following transformations:a) Convert tert-butyl bromide into a primary alkyl halideb) Convert 2-bromopropane into 1-bromopropane
Consider the structure of ozone:Ozone is formed in the upper atmosphere, where it absorbs short-wavelength UV radiation emitted by the sun, thereby protecting us from harmful radiation. Draw all significant resonance structures for ozone (Hint : Begin by drawing all lone pairs).
A mixture of sulfuric acid and nitric acid will produce small quantities of the nitronium ion (NO2+):Does the nitronium ion have any significant resonance structures? Why or why not? o=Ñ=o:
Identify which compounds below possess a molecular dipole moment and indicate the direction of that dipole moment:a.b.c.d. :Çi: ċi: .CI: Н II .C. Н .C. H. :ö: 一 一エ :Cl: Н. н .C. .C. di: Н °. CHO
When an acyl peroxide undergoes homolytic bond cleavage, the radicals produced can liberate carbon dioxide to form alkyl radicals:Using this information, provide a mechanism of formation for each of the following products: ö: R + CO2 or hv R2 An acyl peroxide
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