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organic chemistry
Organic Chemistry 1st edition David R. Klein - Solutions
Draw a Lewis structure for a compound with molecular formula C4H11N in which three of the carbon atoms are bonded to the nitrogen atom. What is the geometry of the nitrogen atom in this compound? Does this compound exhibit a molecular dipole moment? If so, indicate the direction of the dipole
Predict the geometry of each atom except hydrogen in the compounds below:a.b.c.d. Н—с—ҫ—с—с-н -т I—0—т I—0—т Ф:0—I Н Н—О—с—С—с—н нннн
Draw a Lewis dot structure for each of the following compounds:a. CH3CH2OHb. CH3CN
For each pair of compounds below, identify the one that would be expected to have more ionic character. Explain your choice.a) NaBr or HBr b) BrCl or FCl
For each compound below, identify any polar covalent bonds, and indicate the direction of the dipole moment using the symbols δ+ and δ-:a. HBrb. HClc. H2Od. CH4O
There are nine constitutional isomers with molecular formula C7H16.(a) Draw a bond-line structure for all isomers that fit the following criteria: the parent = pentane, and there are two methyl groups connected to the parent.(b) Draw a bond-line structure for the isomer that fits the following
Draw structures for all constitutional isomers with the molecular formula C4H8 that have:a. Only single bondsb. One double bond
Draw structures for all constitutional isomers with the following molecular formulas:a. C4H10b. C5H12c. C6H14d. C2H5Cle. C2H4Cl2f. C2H3Cl3
Arrange the following compounds in order of increasing boiling point: н нн н н н ннн нннн Н-с, С—н -С—С—Н Н—С—С—с—С—ӧ—н Н—с—с— Н—с н нн н С —н Н Н Н Н нн нн Н ннн ннн нн Н-С, нн Н—с—с—с—Н Н—с
For each of the following pairs of compounds, identify the higher boiling compound and justify your choice:a.b.
Bonds between carbon and oxygen (C – O) are more polar than bonds between sulfur and oxygen (S – O). Nevertheless, sulfur dioxide (SO2) exhibits a dipole moment while carbon dioxide (CO2) does not. Explain this apparent anomaly.
For each of the following compounds, identify all groups that would be considered substituents, and then indicate how you would name each substituent.(a)(b)(c)(d)(e)(f)(g)
There are 18 constitutional isomers with molecular formula C8H18. Without drawing all 18 isomers, determine how many of the isomers will have a parent name of heptane.
There are five constitutional isomers with molecular formula C6H14. Draw a bond-line structure for each isomer and identify the parent in each case.
Identify the two compounds below that have the same parent:
Identify and name the parent in each of the following compounds:(a)(b)(c)(d)(e)(f)(g)(h)(i)
In each of the following cases, identify whether the reagent shown is suitable to accomplish the task described. Explain why or why not.(a) To protonateusing H2O(b) To protonateusing(c) To deprotonateusing(d) To protonateusing H2O(e) To protonateusing H2O(f) To protonateusing OZ
As we will learn in Chapter 21, treating a lactone (a cyclic ester) with sodium hydroxide will initially produce an anion:This anion rapidly undergoes an intramolecular proton transfer, in which the negatively charged oxygen atom abstracts the nearby acidic proton. Draw the product of this
Predict the position of equilibrium for each of the following reactions:(a)(b)(c) HO NH NH2 ОН
Amphotericin B is a powerful antifungal agent used for intravenous treatment of severe fungal infections. Identify the most acidic proton in this compound: ОН ОН Он он ОН ОН ОН Но, ОН Он н Amphotericin B NH2 ОН
The following compound is one of the strongest known acids:(a) Explain why it is such a strong acid.(b) Suggest a modification to the structure that would render the compound even more acidic. Н II N-S-CF3 N=S=N F3C-S-N. `CF3 O: F3C
For each pair of compounds below, predict which will be more acidic:(a) HCl HBr(b) H2O H2S(c) NH3 CH4(d)(e) н— —н н н Он ОН Он Cl,C Cl3
In each compound below, two protons are clearly identified. Determine which of the two protons is more acidic.(a)(b)(c)(d)(e)(f)(g)(h)(i) Он Н н н
Amines contain C-N single bonds, while imines contain C - N double bonds: Н Н :N Н Amine Imine
Identify the most acidic proton in each of the following compounds: Xo Xx
Identify which of the following compounds is more acidic. Explain your choice. Н Н C=C H-сЕс-н Н н Н
Consider the two protons highlighted in the following compound:Do you expect these protons to be equivalent, or is one proton more acidic than the other? Explain your choice. CI. F TH. Н
Consider the structure of 2,3-dichloropropanoic acid:This compound has many constitutional isomers.(a) Draw a constitutional isomer that is slightly more acidic and explain your choice.(b) Draw a constitutional isomer that is slightly less acidic and explain your choice.(c) Draw a constitutional
For each pair of compounds below, identify which compound is more acidic and explain your choice:(a)
Identify the most acidic proton in each of the following compounds and explain your choice:(a)(b) 0-H F3C 0-H CI. CI ОН но
In the following compound two protons are clearly identified. Determine which of the two is more acidic. After comparing the conjugate bases, you should get stuck on the following question: Is it more stabilizing for a negative charge to be spread out over one oxygen atom and three carbon atoms or
Ascorbic acid (vitamin C) does not contain a traditional carboxylic acid group, but it is, nevertheless, still fairly acidic (pKa = 4.2). Identify the acidic proton, and explain your choice using resonance structures, if necessary. Он но но ОН Ascorbic acid (Vitamin C)
In each compound below, two protons are clearly identified. Determine which of the two protons is more acidic.(a)(b)(c)(d)(e)(f) Н Н -N Н Н
Nitrogen and sulfur are neither in the same row nor in the same column of the periodic table. Nevertheless, you should be able to identify which proton below is more acidic. Explain your choice: .S. H. エーZ
In each compound below, two protons are clearly identified. Determine which of the two protons is more acidic.(a)(b)(c)(d) Н Н Н Н—С—N' C- Н н
Amino acids, such as glycine, are the key building blocks of proteins and will be discussed in greater detail in Chapter 25. At the pH of the stomach, glycine exists predominantly in aprotonated form in which there are two acidic protons of interest. The pKavalues for these protons are shown.
Hydroxide is not a suitable base for deprotonating acetylene:Explain why not. Can you propose a base that would be suitable? Н—СЕС-Н Н-СЕС: :Он Н-ӧ—н Acetylene Hydroxide
Determine the position of equilibrium for each acid-base reaction below:(a)(b)(c)(d) Н Он н `H. н Oон + H20
Consider the following pKa values, and then answer the following questions:(a) For the following compound, will the lone pair on the nitrogen atom be more or less basic than the lone pair on the oxygen atom?(b) Fill in the blanks: the lone pair on the ____________ atom is ____________ orders of
The following compound has three nitrogen atoms:Each of the nitrogen atoms exhibits a lone pair that can function as a base (to abstract a proton from an acid). Rank these three nitrogen atoms in terms of increasing base strength using the following information: :z エーZ: エーZ: Н N-H le
For each pair of compounds below, identify the stronger base:(a)(b)(c)(d)(e)(f) н Н-СЕС н
L-dopa is used in the treatment of Parkinson€™s disease. Using the follwoing table, identify the four most acidic protons in the compound, and then arrange them in order of increasing acidity (two of the protons will be very similar in acidity and difficult to distinguish at this point in
Propanolol is an antihypertensive agent (used to treat high blood pressure). Using the following table, identify the two most acidic protons in the compound, and indicate the approximate expected pKafor each proton:
For each pair of compounds below, identify the more acidic compound:(a)(b)(c)(d)(e)(f) нон (b) Н Н Н—С—с—н C—н (d) н н H. Н Н Н-о—S—о—Н Н—с—с—н Н-С3с-н (f) Н Н Xи H' `H.
In an intramolecular proton transfer reaction, the acidic site and the basic site are tethered to the same molecule, and a proton is passed from the acidic region of the molecule to the basic region of the molecule, as shown below:Draw a mechanism for this process. Н. н :ö еб: о: eö: :ö, :ö
Each of the following mechanisms contains one or more errors€”that is, the curved arrows may or may not be correct. In each case, identify the errors and then describe what modification would be necessary in order to make the curved arrows correct. Explain your suggested modification in each
All of the following acid-base reactions are reactions that we will study in greater detail in the chapters to follow. For each one, draw the mechanism and then clearly label the acid, base, conjugate acid, and conjugate base:(a)(b)(c)(d) Н eон Н H. H.
Identify any formal charges in the following structures:a.b.c.d. -N=N:
Identify the number of carbon atoms and hydrogen atoms in the compound below:
Which of the following drawings is not a resonance structure for 1-nitrocyclohexene? Explain why it cannot be a valid resonance structure.a.b.c.d. 0- N' Oz-
What is the molecular formula for each compound in the previous problem?Previous problema.b.c. HO
Write a condensed structural formula for each of the following compounds:a.b.c. HO
Draw all significant resonance structures for each of the following compounds:a.b.c. Он н N' z-
Each compound below exhibits one lone pair. In each case, identify the type of atomic orbital in which the lone pair is contained.a.b.c. .N.
Learning to extract structural information from molecular formulas:a) Write out the molecular formula for each of the following compounds:Compare the molecular formulas for the above compounds and fill in the blanks in the following sentence: The number of hydrogen atoms is equal to __________
Draw significant resonance structures for the following compound:
Identify the formal charge in each case below: :N :ö: .N.
How many lone pairs are found in the structure of vitamin C?
Draw bond-line structures for vitamin A and vitamin C: Н Н. н Н н 1н нн н С-нн Нн нн Н Н ннн Н Vitamin A но. нн Но. C=Ć он н но Vitamin C
Draw bond-line structures for all constitutional isomers of C5H12?
Draw bond-line structures for all constitutional isomers of C4H10?
Draw all carbon atoms, hydrogen atoms, and lone pairs for the following compounds: HO HO Acetylsalicylic acid (aspirin) Acetaminophen (Tylenol) N. Caffeine HIN
Isoniazid is used in the treatment of tuberculosis and multiple sclerosis. Identify each lone pair as either localized or delocalized. Justify your answer in each case.
Nicotine is a toxic substance present in tobacco leaves.There are two lone pairs in the structure of nicotine. In general, localized lone pairs are much more reactive than delocalized lone pairs. With this information in mind, do you expect both lone pairs in nicotine to be reactive? Justify your
For each compound below, identify all lone pairs and indicate whether each lone pair is localized or delocalized. Then, use that information to determine the hybridization state and geometry for each atom that exhibits a lone pair.a.b.c.d.e.f. H2N `NH2 z.
Use resonance structures to help you identify all sites of high electron density (δ-) in the following compound: Он
Use resonance structures to help you identify all sites of low electron density (δ+) in the following compound:
Draw all significant resonance structures for each of the following compounds:a.b.c.d.e.f.g.h.i.j.k.l. .Н z: N.
Draw resonance structures for each of the following compounds:a.b.c.d.e.f.g.h.i.j. OH
Fingolimod is a novel drug that has recently been developed for the treatment of multiple sclerosis. In April of 2008, researchers reported the results of phase III clinical trials of fingolimod, in which 70% of patients who took the drug daily for three years were relapse free. This is a
Draw a resonance structure of the compound shown below, called 2-heptanone, which is found in some kinds of cheese.
Draw a resonance structure of the compound below, which was isolated from the fruits of Ocotea corymbosa, a native plant of the Brazilian Cerrado. Он
Draw a resonance structure for each of the compounds below.a.b.c. N°
For each of the compounds below, locate the lone pair adjacent to a positive charge and draw the resonance structure:a.b.c. N.
Draw the resonance structure(s) for each of the compounds below:a.b.c.d.
For each of the compounds below, locate the pattern we just learned (lone pair next to a π bond) and draw the appropriate resonance structure:a.b.c.d.e.f.g.h. NH2
In each case below, draw the curved arrow(s) required in order to convert the first resonance structure into the second resonance structure. In each case, begin by drawing all lone pairs, and then use the formal charges to guide you.a.b.c.d. N. Zo
For each of the structures below, draw the resonance structure that is indicated by the curved arrows. Be sure to include formal charges.a.b.c.d.e.f.g.h. N-
Drawing the resonance structure of the following compound requires one curved arrow. The head of this curved arrow is placed on the oxygen atom, and the tail of the curved arrow can only be placed in one location without violating the rules for drawing curved arrows. Draw this curved arrow.
For each of the problems below, determine whether each curved arrow violates either of the two rules, and describe the violation, if any. (Don€™t forget to count all hydrogen atoms and all lone pairs.)a.b.c.d.e.f.g.h.i.j.k.l. н Н
Troglitazone, rosiglitazone, and pioglitazone, all antidiabetic drugs introduced to the market in the late 1990s, are believed to act on the same receptor(a) Based on these structures, try to identify the likely pharmacophore that is responsible for the antidiabetic activity of these drugs.(b)
Amino acids are biological compounds with the following structure, where the R group can vary. The structure and biological function of amino acids will be discussed in Chapter 25. Identify the total number of lone pairs present in an amino acid, assuming that the R group does not contain any atoms
Identify the number of lone pairs in each of the following compounds:a.b.c.d.
Each of the following compounds contains both oxygen and nitrogen atoms. Identify all lone pairs in each of the following compounds:a.b.c.d.e.f. N. O=C=N
Draw all lone pairs on each of the nitrogen atoms in the compounds below. First, review in the following table, and then come back to these problems. Try to identify all lone pairs without having to count. Then, count to see if you were right.a.b.c.d.e.f.g.h. No Charge 3 bonds + 1 lone pair 2 bonds
A carbene is a highly reactive intermediate in which a carbon atom bears a lone pair and no formal charge:How many hydrogen atoms are attached to the central carbon atom above?
Draw all lone pairs on each of the oxygen atoms in the compounds below. Before doing this, review in the following table, and then come back to these problems. Try to identify all lone pairs without having to count. Then, count to see if you were right.a.b.c.d.e.f.g.h.i.j. No Charge 3 bonds + 1
For each of the compounds below determine whether any of the oxygen atoms bear a formal charge:a.b.c.d. :ö:
For each of the compounds below determine whether any of the nitrogen atoms bear a formal charge:a.b.c.d. N.
Atenolol and enalapril are drugs used in the treatment of heart disease. Both of these drugs lower blood pressure (albeit in different ways) and reduce the risk of heart attack. Using the following table, identify and label all functional groups in these two compounds: NH2 'N' ОН Atenolol N. 'N'
In each of the following compounds, identify all carbon atoms that you expect will be deficient in electron density (δ+). If you need help, refer to Section 1.5.a.b.c.Refer section 1.5€¢ Bonds are classified as (1) covalent, (2) polar covalent, or (3) ionic.€¢ Polar
Draw bond-line structures for all constitutional isomers of the following compound:CH3CH2CH(CH3)2
Draw a bond-line structure for each of the following compounds:a.b.c.d. (CH3)3C €“ C(CH3)3 e. CH3CH2CH(CH3)2 f. (CH3CH2)3COHg. (CH3)2CHCH2OH h. CH3CH2CH2OCH3 i. (CH3CH2)2C = CH2j. CH2 = CHOCH2CH(CH3)2 k. (CH3CH2)2CHCH2CH2NH2l. CH2 =
Identify whether each transformation below involves an increase, a decrease, or no change in the number of hydrogen atoms:a.b.
Each transformation below shows a starting material being converted into a product (the reagents necessary to achieve the transformation have not been shown). For each transformation, determine whether the product has more carbon atoms, fewer carbon atoms, or the same number of carbon atoms as the
Draw a plausible mechanism for each of the following transformations:(a)(b)(c)(d)(e)(f) нн CHs `H + H3C Hас снз H30* но OCH3 H. Н,о
A ketone with molecular formula C9H18O exhibits only one signal in its 1H NMR spectrum. Provide a systematic (IUPAC) name for this compound.
A compound with molecular formula C13H10O produces a strong signal at 1660 cmˆ’1in its IR spectrum. The13C NMR spectrum for this compound is shown below. Identify the structure of this compound. Carbon 13 NMR -130.0 -128.3 132.4- 137.5- -196.7 200 180 170 160 150 Chemical Shift (ppm) 140
A compound with molecular formula C9H10O exhibits a strong signal at 1687 cmˆ’1in its IR spectrum. The1H and13C NMR spectra for this compound are shown below. Identify the structure of this compound. Proton NMR 2 3 4 Chemical Shift (ppm) Carbon 13 NMR 128.3 -127.7 132.5- 31.3- 7.9- -199.9
An aldehyde with molecular formula C4H6O exhibits an IR signal at 1715 cm−1.(a) Propose two possible structures that are consistent with this information.(b) Describe how you could use 13C NMR spectroscopy to determine which of the two possible structures is correct.
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