Organic Chemistry 2nd Edition solutions

Organic Chemistry 2
Draw a bond-line structure for each of the following compounds: (a) C C C H H H H H H H C H H C C H H H C H H H C H H H (b) O H C H C H H H C H H C C H H H (c) OH HO C OH C C H H H H H (d) (CH3)3C!C(CH3)3 (e) CH3CH2CH(CH3)2 (f) (CH3CH2)3COH (g) (CH3)2CHCH2OH (h) CH3CH2CH2OCH3 (i) (CH3CH2)2CRCH2 (j) C

Organic Chemistry 2
Draw bond-line structures for all constitutional isomers of the following compound: CH3CH2CH(CH3)2

Organic Chemistry 2
0 In each of the following compounds, identify all carbon atoms that you expect will be deficient in electron density (d+). If you need help, refer to Section 1.5. (a) O Br H (b) O O (c) Cl O

Organic Chemistry 2
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 Table 2.1, identify and label all functional groups in these two compounds: Atenolol Enalapril O OH N O O H N HO O O

Organic Chemistry 2
2 For each of the following structures determine whether any of the nitrogen atoms bear a formal charge: (a) N (b) N (c) N (d) N

Organic Chemistry 2
For each of the following structures determine whether any of the oxygen atoms bear a formal charge: (a) O (b) O (c) O (d) O H H H

Organic Chemistry 2
Draw all lone pairs on each of the oxygen atoms in the following structures. Before doing this, review Table 2.2 and then come back to these problems. Try to identify all lone pairs without having to count. Then, count to see if you were correct. (a) O (b) O O (c) OH O (d) O O @ (e) O@ (f) O (g) O H

Organic Chemistry 2
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?

Organic Chemistry 2
Draw all lone pairs on each of the nitrogen atoms in the following structures. First, review Table 2.3 and then come back to these problems. Try to identify all lone pairs without having to count. Then, count to see if you were correct. (a) N (b) N H (c) N (d) N! (e) N @ (f) N (g) N ! (h) N H ! NH2

Organic Chemistry 2
Each of the following structures contains both oxygen and nitrogen atoms. Identify all lone pairs associated with those atoms.a)ON! H(b) O C N@(c) O N O! (d)NO ! O @ (e) NH2O (f) O C N

Organic Chemistry 2
Identify the number of lone pairs in each of the following structures: (a) @ (b) ! (c) @ (d) O O @

Organic Chemistry 2
Amino acids are biological compounds with the following structure,where the R group can vary. The structure and biological functionof amino acids will be discussed in Chapter 25. Identify the total numbof lone pairs present in an amino acid, assuming that the R groupdoes not contain any atoms with lo

Organic Chemistry 2
Troglitazone, rosiglitazone, and pioglitazone, all antidiabetic drugs introduced to the market in the late 1990s, are believed to act on the same receptor: Troglitazone S N O O H O O HO Rosiglitazone S N O O H O N N Pioglitazone S N O O H O N (a) Based on these structures, try to identify the likely

Organic Chemistry 2
For each of the problems below, determine whether each curved arrow violates either of the two rules and describe the violation, if any. (Dont forget to count all hydrogen atoms and all lone pairs.) (a) N H H ! (b) O (c) OH (d) O H (e) O H (f) (g) (h) O (i) N C (j) H3C N N ! (k) O R (l) N

Organic Chemistry 2
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. O

Organic Chemistry 2
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) O O (d) N @ (e) OH (f) O O N ! @ (g) O O N ! @ (h) O

Organic Chemistry 2
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) O O ! @ (b) O O ! @ (c) N O O N @ @ (d) ! !

Organic Chemistry 2
For each of the compounds below, locate the pattern we just learned (lone pair next to a p bond) and draw the appropriate resonance structure: (a) O O (b) @ (c) O (d) NH2 (e) O N O @ ! (f) O@ (g) N Acetylcholine (a neurotransmitter) O O ! (h) 5-Amino-4-oxopentanoic acid (used in therapy and diagnosis

Organic Chemistry 2
Draw the resonance structure(s) for each of the compounds below: (a) ! (b) ! (c) ! (d) !

Organic Chemistry 2
For each of the compounds below, locate the lone pair adjacent to a positive charge and draw the resonance structure: (a) N ! (b) N @ ! (c) O !

Organic Chemistry 2
Draw a resonance structure for each of the compounds below. (a) N (b) O (c) O

Organic Chemistry 2
Draw a resonance structure of the compound below, which was isolated from the fruits of Ocotea corymbosa, a native plant of the Brazilian Cerrado. OH O

Organic Chemistry 2
Draw a resonance structure of the compound shown below, called 2-heptanone, which is found in some kinds of cheese. O

Organic Chemistry 2
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 tremendous

Organic Chemistry 2
Draw resonance structures for each of the following compounds: (a) O (b) ! (c) @ (d) O O (e) O ! (f) O (g) N ! (h) N (i) N O (j) Cl O

Organic Chemistry 2
Draw all significant resonance structures for each of the following compounds: (a) N H (b) N (c) N@ (d) O C N (e) S O (f) @ (g) O (h) ! (i) O @ (j) C N @ (k) C N (l) OH !

Organic Chemistry 2
Use resonance structures to help you identify all sites of low electron density (d+) in the following compound: Step 2 Identify if the resonance structure is significant by inspecting the number of charges and the number of electrons on heteroatoms. Step 3 Repeat steps 1 and 2 to identify any other s

Organic Chemistry 2
Use resonance structures to help you identify all sites of high electron density (d-) in the following compound: OH

Organic Chemistry 2
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) H2N NH2 (b) O N O (c) O OH H2N NH2 (d) N (e) N H (f) O O O

Organic Chemistry 2
Nicotine is a toxic substance present in tobacco leaves. Nicotine N N 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? Ju

Organic Chemistry 2
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. Isoniazid N N O NH2 H

Organic Chemistry 2
Draw all carbon atoms, hydrogen atoms, and lone pairs for the following compounds: O OH O O HO N O H Caffeine N N N N O O Acetaminophen (Tylenol) Acetylsalicylic acid (aspirin)

Organic Chemistry 2
Draw bond-line structures for all constitutional isomers of C4H10.

Organic Chemistry 2
Draw bond-line structures for all constitutional isomers of C5H12.

Organic Chemistry 2
Draw bond-line structures for vitamin A and vitamin C: Vitamin A C C C C C C C C C C C C C C C C C C C O H H H H H H H H C H H H H H H H H H H H H H H H H H H H H H H Vitamin C C C C O C HO OH C O C HO HO H H H H

Organic Chemistry 2
How many lone pairs are found in the structure of vitamin C?

Organic Chemistry 2
Identify the formal charge in each case below: O N N O O N

Organic Chemistry 2
Draw significant resonance structures for the following compound: O

Organic Chemistry 2
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 __________ tim

Organic Chemistry 2
7 Each compound below exhibits one lone pair. In each case, identify the type of atomic orbital in which the lone pair is contained. (a) N ! (b) @ (c) N !

Organic Chemistry 2
Draw all significant resonance structures for each of the following compounds: (a) N OH H ! (b) O ! (c) !

Organic Chemistry 2
Write a condensed structural formula for each of the following compounds: (a) (b) OH (c)

Organic Chemistry 2
What is the molecular formula for each compound in the previous problem?

Organic Chemistry 2
Which of the following drawings is not a resonance structure for 1-nitrocyclohexene? Explain why it cannot be a valid resonance structure. (a) O N ! O @ (b) N O ! O@ (c) N O O ! ! @ @ (d) N OO

Organic Chemistry 2
Identify the number of carbon atoms and hydrogen atoms in the compound below:

Organic Chemistry 2
Identify any formal charges in the following structures: (a) O (b) N N (c) O (d) N

Organic Chemistry 2
Draw bond-line structures for all constitutional isomers with molecular formula C4H9Cl.

Organic Chemistry 2
Draw resonance structures for each of the following: (a) O (b) O ! (c) ! (d) N (e) NH2 (f) @ (g) O (h) O O (i) OH ! (j) O !

Organic Chemistry 2
Determine the relationship between the two structures below. Are they resonance structures or are they constitutional isomers? O O @

Organic Chemistry 2
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)

Organic Chemistry 2
Draw a bond-line structure for each of the following compounds: (a) \(CH_2=CHCH_2C(CH_3)_3\) (b) \((CH_3CH_2)_2CHCH_2CH_2OH\) (c) \(CH\equiv COCH_2CH(CH_3)_2\) (d) \(CH_3CH_2OCH_2CH_2OCH_2CH_3\) (e) \((CH_3CH_2)_3CBr\) (

Organic Chemistry 2
A mixture of sulfuric acid and nitric acid will produce small quantities of the nitronium ion (NO2 +): O N O ! Does the nitronium ion have any significant resonance structures? Why or why not?

Organic Chemistry 2
Consider the structure of ozone: O O O @ ! Ozone is formed in the upper atmosphere, where it absorbs shortwavelength 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.)

Organic Chemistry 2
Melatonin is an animal hormone believed to have a role in regulatingthe sleep cycle:The structure of melatonin incorporates twonitrogen atoms. What are the hybridizationstate and geometry of each nitrogen atom?Explain your answer.n N N O OCH3 H H Melatonin

Organic Chemistry 2
Draw all significant resonance structures for each of the following compounds: Estradiol (Female sex hormone) Testosterone (Male sex hormone) HO OH H H H O OH H H H

Organic Chemistry 2
Cycloserine is an antibiotic isolated from the microbe Streptomyces orchidaceous. It is used in conjunction with other drugs for the treatment of tuberculosis. Cycloserine O N O H NH2 (a) What is the molecular formula of this compound? (b) How many sp3 -hybridized carbon atoms are present in this str

Organic Chemistry 2
Ramelteon is a hypnotic agent used in the treatment of insomnia: Ramelteon O N H O (a) What is the molecular formula of this compound? (b) How many sp3 -hybridized carbon atoms are present in this structure? (c) How many sp2 -hybridized carbon atoms are present in this structure? (d) How many sp-hybr

Organic Chemistry 2
In the compound below, identify all carbon atoms that are electron deficient (d+) and all carbon atoms that are electron rich (d-). Justify your answer with resonance structures. H OH H O

Organic Chemistry 2
Consider the following two compounds: Compound A Compound B O O O O (a) Identify which of these two compounds has greater resonance stabilization. (b) Would you expect compound C (below) to have a resonance stabilization that is more similar to compound A or to compound B? Compound C O O

Organic Chemistry 2
Single bonds generally experience free rotation at room temperature (as will be discussed in more detail in Chapter 4): Free rotation of single bond Nevertheless, the single bond shown below exhibits a large barrier to rotation. In other words, the energy of the system is greatly increased if that bo

Organic Chemistry 2
Polymers are very large compounds, assembled from smaller units, called monomers. For example, polymer 2, called poly(vinyl acetate), is made from vinyl acetate (1). Polymer 2 can be converted to polymer 4, called poly(vinyl alcohol), or PVA, via a process called hydrolysis (explored further in Chapt

Organic Chemistry 2
Coumarin and its derivatives exhibit a broad array of industrial applications, including, but not limited to, cosmetics, food preservatives, and fluorescent laser dyes. Some derivatives of coumarin, such as warfarin, exhibit antithrombic activity and are currently used as blood thinners (to prevent t

Organic Chemistry 2
CL-20 and HMX are both powerful explosives. CL-20 produces a more powerful blast but is generally considered too shock-sensitive for practical use. HMX is significantly less sensitive and is used as a standard military explosive. When a 2:1 mixture of the two compounds is cocrystallized, the resultin

Organic Chemistry 2
Progesterone is a female hormone that plays a critical role in the menstrual cycle by preparing the lining of the uterus for implantation of an egg. During W. S. Johnsons biomimetic synthesis of progesterone (a synthesis that draws inspiration from and mimics naturally occurring, biosynthetic pathway

Organic Chemistry 2
Many compounds with desirable medicinal properties are isolated from natural sources and are thus referred to as natural products. However, a compounds medicinal properties are often known before the structure of the compound has been determined. Below are examples of compounds where the first propos

Organic Chemistry 2
The following compound is an intermediate in the synthesis of a gelator, which is a compound capable of self-assembling to form a gel in an organic liquid (Soft Matter 2012, 8, 54865492). N O H O(CH2)11CH3 O CH3(CH2)11O CH3(CH2)11O H (a) Identify each functional group in the molecule. (b) In Chapter

Organic Chemistry 2
The reaction between an aldehyde and an amine results in the formation of a functional group called an imine, as shown in the following general reaction: + O R R NH2 N R R An imine Consider the reactants AD, which have been used in the synthesis of novel self-assembling molecules with unique and dyna

Organic Chemistry 2
The following compound is an amino acid derivative (Chapter 25). In solution, molecules of this compound show a tendency to stick together, or self-assemble, via a series of intermolecular hydrogen bonds. During self-assembly, the growing aggregate can entrap molecules of liquid, thereby forming a ge

Organic Chemistry 2
In Chapter 3, we will explore the factors that render compounds acidic or basic. Tropolone (1) is a compound that is both fairly acidic and fairly basic (J. Org. Chem. 1997, 62, 32003207). It is acidic because it is capable of losing a proton (H+) to form a relatively stable anion (2), while it is ba

Organic Chemistry 2
Triphenylmethane dyes are among the first synthetic dyes developed for commercial use. A comparison of the structures of these compounds reveals that even small differences in structure can lead to large differences in color (Chem. Rev. 1993, 93, 381433). The structures of three such dyes are shown b

Organic Chemistry 2
Basic red 1 is a tetracyclic compound (it has four rings) that shares many structural similarities with the dyes in the previous problem (Chem. Rev. 1993, 93, 381433). This compound has many significant resonance structures, and the positive charge is highly delocalized. While resonance structures ca