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organic chemistry
Organic Chemistry 1st edition David R. Klein - Solutions
Consider the following four energy diagrams:(a) Which diagrams correspond with a two-step mechanism?(b) Which diagrams correspond with a one-step mechanism?(c) Compare energy diagrams A and C. Which has a relatively larger Ea?(d) Compare diagrams A and C. Which has a negative ΔG?(e)
Consider the following reaction:(a) Use Table 6.1 to estimate ΔH for this reaction.(b) ΔS of this reaction is positive. Explain.(c) Determine the sign of ΔG.(d) Is the sign of ΔG dependent on temperature?(e) Is the magnitude of ΔG
In each of the following cases compare the bonds identified with red arrows, and determine which bond you would expect to have the largest bond dissociation energy:a.b. CI .F Br
For each of the following carbocations determine if it will rearrange, and if so, draw the carbocation rearrangement with a curved arrow:a.b.c.d.e.f.g.h.
Draw the curved arrows that accomplish each of the following transformations:a.b.c. Н о—н H. Н о—н ОН н H. н нен
The following two reactions will be explored in different chapters. Yet, they are very similar. Identify and compare the sequences of arrow-pushing patterns for the two reactions.Reaction 1Reaction 2 -:Он нӧ. он :ОН Lö:0 e.. :Он -:Ci: :CI: C! :OH :ОН
For each of the following multistep reactions, read the curved arrows and identify the sequence of arrow€“pushing patterns:a.b.c.d.e. :OH 는노동보송 0=s=0. :ÖH 0=s=0: o=s=0:
Identify which arrow-pushing pattern is utilized in the following step:
Each of the following compounds exhibits two electrophilic centers. Identify both centers in each compound. (You will need to draw resonance structures in each case.)a.b.c. H. A cockroach repellant found in cucumbers Nootkatone Found in grapefruits
The following hypothetical compound cannot be prepared or isolated, because it has a very reactive nucleophilic center and a very reactive electrophilic center, and the two sites would react with each other rapidly. Identify the nucleophilic center and electrophilic center in this hypothetical
Identify all of the electrophilic centers in each of the following compounds:a.b.c. ОН Arachidonic acid A precursor in the biosynthesis of many hormones 2-Heptanone Used to control the population of Varroa mites in honey bee colonies
Consider the relative energy diagrams for four different processes:(a) Compare energy diagrams A and D. Assuming all other factors (such as concentrations and temperature) are identical for the two processes, identify which process will occur more rapidly. Explain.(b) Compare energy diagrams A and
In each of the following cases, use the data given to determine whether the reaction favors reactants or products:(a) A reaction for which ΔG = +1.52 kJ/mol(b) A reaction for which Keq = 0.5(c) A reaction carried out at 298 K, for which ΔH = +33 kJ/mol and ΔS = +150 J/mol · K(d) An exothermic
At room temperature, molecules spend most of their time in lower energy conformations. In fact, there is a general tendency for any system to move toward lower energy. As another example, electrons form bonds because they “prefer” to achieve a lower energy state. We can now appreciate that the
For each of the following processes predict the sign of ΔS for the reaction. In other words, will ΔSsysbe positive (an increase in entropy) or negative (a decrease in entropy)?a.b.c.d.e.f. ||
Using the data in the following table, predict the sign and magnitude of ΔH° for each of the following reactions. In each case, identify whether the reaction is expected to be endothermic or exothermic:a.b.c.d. KJ/MOL KCAL/MOL к./мOL KCAL/MOL кJ/мOL KCAL/мOL Нас—сн сHз
As mentioned in problem 5.58, some molecules are chiral even though they lack a chirality center. For example, consider the following two compounds shown, and explain the source of chirality in each case:a.b. PPH2 PPH2 (S)-BINAP
Based on your analysis in the previous problem, determine whether the following allene is expected to be chiral: Me Мель, Me, c=c=c н Me
It is possible for a compound to be chiral even though it lacks a carbon atom with four different groups. For example, consider the structure of the following compound which belongs to a class of compounds called allenes. This allene is chiral. Draw its enantiomer, and explain why this compound is
For each of the following pairs of compounds, determine the relationship between the two compounds.a.b. Et Н н Me Н Me
Draw a Fischer projection for each of the following compounds, placing the €”CO2H group at the top.a.b.c. ОН но. Но. Он ОН Но ОН ОН ОН
The following questions apply to the five compounds in Problem 5.54.(a) Which compound is meso?(b) Would an equal mixture of compounds b and c be optically active?(c) Would an equal mixture of compounds d and e be optically active?
Identify the hybridization state and geometry of each carbon atom in benzene. Use that information to determine the geometry of the entire molecule: .C: н H. .C. Н н Н Benzene
For each of the following pairs of compounds, determine the relationship between the two compounds:a.b.c.d.e.f.g.h.i.j.k.l. Br Br
Classify each of the following compounds below as cis, trans, or not stereo-isomeric: но, Но но, НО Он
Identify whether each of following pairs of compounds are enantiomers or diastereomers:a.b.c.d.e.f. OH OH .CI CI
The specific rotation of l-alanine in water (at 25°C) is +2.8. A chemist prepared a mixture of l-alanine and its enantiomer, and 3.50 g of the mixture was dissolved in 10.0 mL of water. This solution was then placed in a sample cell with a path length of 10.0 cm and the observed rotation was
The specific rotation of vitamin B7 in water (at 22°C) is +92. A chemist prepared a mixture of vitamin B7 and its enantiomer, and this mixture had a specific rotation of +85. Calculate the % ee of this mixture.
The specific rotation of ephedrine in ethanol (at 20°C) is -6.3. A chemist prepared a mixture of ephedrine and its enantiomer, and this mixture had a specific rotation of -6.0. Calculate the % ee of this mixture.
Which of the following compounds has the larger dipole moment? Explain your choice:CHCl3 or CBrCl3
Identify whether each of the following compounds exhibits a molecular dipole moment. For compounds that do, indicate the direction of the net molecular dipole moment:a. CHCl3b. CH3OCH3c. NH3d. CCl2Br2e.f.
Predict the value for the specific rotation of the following compound. Explain your answer. -ОН но, Но.
When 1.30 g of menthol is dissolved in 5.00 mL of ether and placed in a sample cell 10.0 cm in length, the observed rotation at 20°C (using the D line of sodium) is +0.57°. Calculate the specific rotation of menthol.
When 0.095 g of cholesterol is dissolved in 1.00 mL of ether and placed in a sample cell 10.0 cm in length, the observed rotation at 20°C (using the D line of sodium) is -2.99°. Calculate the specific rotation of cholesterol.
When 0.575 g of monosodium glutamate (MSG) is dissolved in 10.0 mL of water and placed in a sample cell 10.0 cm in length, the observed rotation at 20°C (using the D line of sodium) is +1.47°. Calculate the specific rotation of MSG.
Carbon is not the only element that can function as a chirality center. In Problem 5.6 we saw an example in which a phosphorus atom is a chirality center. In such a case, the lone pair is always assigned the fourth priority. Using this information, assign the configuration of the chirality center
Assign the configuration of the chirality center in the following compound:
Each of the following compounds possesses carbon atoms that are chirality centers. Locate each of these chirality centers, and identify the configuration of each one:a.b.c.d.e.f. Он Н Ephedrine A bronchodilator and decongestant obtained from the Chinese plant Ephedra sinica CI -Br CI ČI Br
Ixabepilone is a cytotoxic compound approved by the FDA in 2007 for the treatment of advanced breast cancer. Bristol-Myers Squibb is marketing this new drug under the trade name Ixempra. Draw the enantiomer of this compound: он N. Он Ixabepilone
Draw the enantiomer of each of the following compounds:a.b.c.d.e.f.g. Он Н Но Но Albuterol (sold under the trade name VentolinTM) A bronchodilator used in the treatment of asthma N. он Н Propranolol A beta blocker used in the treatment of hypertension
Do you expect the following compound to be chiral? Explain your answer (consider whether this compound is super-imposable on its mirror image).
Draw all constitutional isomers of C4H9Br, and identify the isomer(s) that possess chirality centers.
Identify all chirality centers in each of the following compounds:a.b.c.d.e.f. ОН Но. но ОН Ascorbic acid (Vitamin C) НО Vitamin D3
Compound X and compound Y are constitutional isomers with molecular formula C5H10. Compound X possesses a carbon-carbon double bond in the trans configuration, while compound Y possesses a carbon-carbon double bond that is not stereo-isomeric:(a) Identify the structure of compound X.(b) Identify
Identify the number of stereo-isomers that are possible for a compound with the following constitution: H2CCHCH2CH2CH2CHCH2.
For each of the following compounds determine whether it exhibits a cis configuration or a trans configuration or whether it is simply not stereo-isomeric.a.b.c.d.e.f.g. F
For each of the following pairs of compounds, identify the compound that would have the higher heat of combustion:(a)(b)(c)(d)
Draw the ring flip for each of the following compounds:(a)(b)(c) OH ČI CI ОН
What are the relative energy levels of the three staggered conformations of 2,3-dimethylbutane when looking down the C2-C3 bond?
Sketch an energy diagram that shows a conformational analysis of 2,2-dimethylpropane. Does the shape of this energy diagram more closely resemble the shape of the energy diagram for ethane or for butane?
Draw each of the following compounds:(a) 2,2,4-Trimethylpentane(b) 1,2,3,4-Tetramethylcycloheptane(c) 2,2,4,4-Tetraethylbicyclo [1.1.0] butane
Identify which of the following compounds is expected to have the larger heat of combustion:
Use a Newman projection to draw the most stable conformation of 3-methylpentane, looking down the C2-C3 bond.
For each of the following pairs of compounds, identify whether the compounds are constitutional isomers or different representations of the same compound:(a)(b)(c)
What is the systematic name for each of the following compounds:(a)(b)(c)(d)
Each of the structures in the previous problem has one or more substituents connected to the parent.(a) Identify the name of each substituent in 4.39a.(b) Identify the common name and the IUPAC name of the complex substituent in 4.39b.(c) Identify the name of each substituent in 4.39c.(d) Identify
Identify the name of the parent for each of the following compounds:(a)(b)(c)(d)
Draw Haworth projections for cis-1,3-di-tert-butylcyclohexane and trans-1,3-di-tert butylcyclohexane. One of these compounds exists in a chair conformation, while the other exists primarily in a twist boat conformation. Offer an explanation.
Draw Haworth projections for cis-1,4-dimethylcyclohexane and trans-1,4-dimethylcyclohexane. Then for each compound, draw the two chair conformations. Use these conformations to determine whether the cis isomer or the trans isomer is more stable.
Draw Haworth projections for cis-1,3-dimethylcyclohexane and trans-1,3-dimethylcyclohexane. Then, for each compound, draw the two chair conformations. Use these conformations to determine whether the cis isomer or the trans isomer is more stable.
Compound A exists predominantly in a chair conformation, while compound B exists predominantly in a twist boat conformation. Explain. Compound A Compound B
You drew the two chair conformations of lindane. Carefully inspect them, and predict the difference in energy between them, if any.
Draw the lowest energy conformation for each of the following compounds:(a)(b)(c)(d)(e)(f) .CI 'CI
Lindane (hexachlorocyclohexane) is an agricultural insecticide that can also be used in the treatment of head lice. Draw both chair conformations of lindane. CI CI 'CI CI ČI Lindane
Draw both conformations for each of the following compounds:(a)(b)(c)(d)(e)(f)(g)(h) Br
The most stable conformation of 5-hydroxy-1,3-dioxane has the OH group in an axial position, rather than an equatorial position. Provide an explanation for this observation. Н
Consider the following chair conformation of bromocyclohexane:(a) Identify whether the bromine atom occupies an axial position or an equatorial position in the conformation above.(b) Draw a bond-line drawing of this chair conformation (without Newman projections).(c) Draw a bond-line drawing of the
Draw both chair conformations for each of the following compounds:(a)(b)(c)(d)(e) Он NH2
In the following compound, identify the number of hydrogen atoms that occupy axial positions as well as the number of hydrogen atoms that occupy equatorial positions:
Practice drawing a chair conformation with all 12 positions (6 axial and 6 equatorial). Practice several times on a blank piece of paper. Repeat until you can draw all 12 positions without looking at the instructions above.
Practice drawing a chair conformation with all six equatorial positions. Repeat until you can draw all six positions without looking at the instructions above.
Practice drawing a chair conformation with all six axial positions. Repeat until you can draw all six positions without looking at the instructions above.
Draw a chair conformation for each of the following compounds:(a)(b) z-
Practice drawing a chair several times using a blank piece of paper. Repeat the procedure until you can do it without looking at the instructions above. For each of your chairs, make sure that it contains three sets of parallel lines.
Compare the three staggered conformations of ethylene glycol. The anti conformation of ethylene glycol is not the lowest energy conformation. The other two, staggered conformations are actually lower in energy than the anti conformation. Suggest an explanation. Он Но Ethylene glycol
In each case below, identify the highest and lowest energy conformations. In cases where two or three conformations are degenerate, draw only one as your answer.(a)(b)(c)(d)
For each of the following compounds, predict the energy barrier to rotation (looking down any one of the C-C bonds). Draw a Newman projection and then compare the staggered and eclipsed conformations. Remember that we assigned 4 kJ/mol to each pair of eclipsing H’s and 6 kJ/mol to an H eclipsing
Determine whether the following compounds are constitutional isomers: Н CHз -Н H3C Н H;C CH3 CH3 Н Н Н
Draw a bond-line structure for each of the following compounds:(a)(b)(c) CHз CHз- CH2CH3 CH CH-CHз н CHз Н. Н CHз
In each case below, draw a Newman projection as viewed from the angle indicated:(a)(b)(c)(d)(e)(f) Observer CI Observer CI
The following table indicates the number of constitutional isomers with molecular formula C7H16. Draw each of the isomers, making sure not to draw the same compound twice. NUMBER OF CONSTITUTIONAL ISOMERS FOR VARIOUS ALKANES MOLECULAR FORMULA NUMBER OF CONSTITUTIONAL ISOMERS CэНв CAH10 CSH12
For each pair of compounds, identify whether they are constitutional isomers or two representations of the same compound:(a)(b)(c)(d)
Draw a bond-line structure for each of the following compounds:(a) 2,2,3,3-Tetramethylbicyclo [2.2.1] heptane(b) 8,8-Diethylbicyclo [3.2.1] octane(c) 3-Isopropylbicyclo [3.2.0] heptane
Name each of the following compounds:(a)(b)(c)(d)(e)(f)(g)(h)(i)
Draw a bond-line drawing for each of the following compounds:(a) 3-Isopropyl-2,4-dimethylpentane(b) 4-Ethyl-2-methylhexane(c) 1,1,2,2-Tetramethylcyclopropane
Provide a systematic name for each of the following compounds below:(a)(b)(c)(d)(e)(f)(g)(h)(i)(j)(k)(l)(m)(n)(o)(p)(q)
Draw all possible alkyl substituents that possess exactly five carbon atoms. Provide a systematic name for each of these substituents.
The following substituent is called a phenyl group:With this in mind, identify the systematic name for each substituent below: Phenyl
For each of the following compounds, identify all groups that would be considered substituents, and then indicate the systematic name as well as the common name for each substituent:(a)(b)(c)(d)(e)
For each pair of compounds below, predict which compound will have the higher boiling point and explain your choice:a) CH3CH2CH2OCH3 or CH3CH2CH2CH2OHb) CH3CH2CH2CH3 or CH3CH2CH2CH2CH3c) ннн Н or С—Н Н—С—С—С—Н
Count the total number of s bonds and p bonds in the compound below: н Н Н—ӧ—с—с-с—С3с—с-N—Н ннн н Н нн
Identify the expected hybridization state and geometry for the central atom in each of the following compounds:a.b.c.d.e. H. н I-z: Н н I-
Predict the bond angles for all bonds in the following compounds:a) CH3CH2OH b) CH2O c) C2H4 d) C2H2e) CH3OCH3 f) CH3NH2 g) C3H8h) CH3CN
For each type of bond below, determine the direction of the expected dipole moment.a) C – O b) C – Mg c) C – N d) C – Lie) C – Cl f) C – H g) O – H h) N – H
Draw structures for any five constitutional isomers with molecular formula C2H6O3?
In the compounds below, classify each bond as covalent, polar covalent, or ionic:a) NaBr b) NaOHc) NaOCH3d) CH3OH e) CH2O
Identify the neutral element that corresponds with each of the following electronic configurations:a) 1s22s22p4b) 1s22s22p5 c) 1s22s22p2d) 1s22s22p3 e) 1s22s22p63s23p5
Determine whether each compound below exhibits a molecular dipole moment:a) CH4 b) NH3 c) H2Od) CO2 e) CCl4 f) CH2Br2
Draw the structure for the only constitutional isomer of cyclopropane: C. н Н. -' Н Н Cyclopropane
Draw a Lewis structure of the anion AlBr4 – and determine its geometry.
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