Organic Chemistry 2nd Edition solutions

Organic Chemistry 2
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: N N O H OH OH OH O F

Organic Chemistry 2
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:NCH3OHOOH

Organic Chemistry 2
Paclitaxel (marketed under the trade name Taxol) is found in the bark of the Pacific yew tree, Taxus brevifolia, and is used in the treatment of cancer: O N O O O O O OH O OH H O O O O OH H

Organic Chemistry 2
Classify each of the following compounds below as cis, trans, or not stereoisomeric: OH HO HO

Organic Chemistry 2
For each of the following pairs of compounds, determine the relationship between the two compounds: (a) (b) O O N CH3 O H O OH (c) Br Br (d) (e) (f) (g) (h) (i) OH OH (j) OH OH (k) Cl Cl Cl Cl (l)

Organic Chemistry 2
Identify the number of stereoisomers expected for each of the following: (a) OH OH Cl (b) OH OH (c) Me Me Cl (d) (e) HO OH (f)

Organic Chemistry 2
Draw the enantiomer for each of the following compounds: (a) Cl OH (b) (c) (d) Et OH (e) Cl Me F OH (f) Cl F (g) H OH H OH CH3 HO H O H (h) HO H H CH2OH O OH OH HO H (i) OH OH Cl Me Cl Me OH O (j) OH (k) OH Cl (l) OH

Organic Chemistry 2
Identify the configuration of each chirality center in the following compounds: (a) Me O Et OH (b) NH2 (c) Cl (d) HO Et Cl (e) O H F (f) Cl Br O H (g) HO (h) H Me OH Me HO H (i) Cl O

Organic Chemistry 2
You are given a solution containing a pair of enantiomers (A and B). Careful measurements show that the solution contains 98% A and 2% B. What is the ee of this solution?

Organic Chemistry 2
For each of the following pairs of compounds, determine the relationship between the two compounds: (a) H CH2OH CH2OH OH HO H HO H HO H O H O H (b) H CH2OH CH2OH OH OH O OH O OH H H OH HO H (c) Cl Cl Cl Cl (d) (e)

Organic Chemistry 2
For each of the following pairs of compounds, determine the relationship between the two compounds: (a) Cl Cl Cl Cl (b) (c) (d) OH Cl Cl OH (e) (f) O Cl Cl O Cl Cl (g)

Organic Chemistry 2
Determine whether each statement is true or false: (a) A racemic mixture of enantiomers is optically inactive. (b) A meso compound will have exactly one nonsuperimposable mirror image. (c) Rotating the Fischer projection of a molecule with a single chirality center by 90 will generate the enantiomer

Organic Chemistry 2
When 0.075 g of penicillamine is dissolved in 10.0 mL of pyridine and placed in a sample cell 10.0 cm in length, the observed rotation at 20C (using the D line of sodium) is -0.47. Calculate the specific rotation of penicillamine.

Organic Chemistry 2
(R)-Limonene is found in many citrus fruits, including oranges and lemons: For each of the following compounds identify whether it is (R)-limonene or its enantiomer, (S)-limonene: (a) (b) (c) (d)

Organic Chemistry 2
Each of the following compounds possesses a plane of symmetry. Find the plane of symmetry in each compound. In some cases, you will need to rotate a single bond to place the molecule into a conformation where you can more readily see the plane of symmetry. (a) (b) HO OH (c) CH3 H3C H Br Br H (d) Cl H

Organic Chemistry 2
cis-1,3-Dimethylcyclobutane has two planes of symmetry. Draw the compound and identify both planes of symmetry.

Organic Chemistry 2
Consider the following two compounds. These compounds are stereoisomers of 1,2,3- trimethylcyclohexane. One of these compounds has three chirality centers, while the other compound has only two chirality centers. Identify which compound has only two chirality centers and explain why

Organic Chemistry 2
For each of the following pairs of compounds, determine the relationship between the two compounds: (a) (b) H Me Cl Me HO H Cl Me H Me HO H (c) OH OH (d) (e) (f) (g) Cl Cl (h) (i) (j) (k) CH3 HO H CH3 CH3 HO H H OH H OH H OH CH3 HO H (l) Et HO H Me Et HO H H OH H OH H OH Me HO H

Organic Chemistry 2
The specific rotation of (S)-carvone (at 20C) 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 20C? (b) Calculate the % ee of this mixture. (c) What percentage of the mixture i

Organic Chemistry 2
Identify whether each of the following compounds is chiral or achiral: (a) (b) Cl (c) (d) OH OH (e) OH OH (f) OH OH (g) Cl Cl (h) Cl Cl (i) (j) OH (k) (l) OH (m) OH (n) (o) (p

Organic Chemistry 2
The specific rotation of vitamin C (using the D line of sodium, at 20C) 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.

Organic Chemistry 2
Determine whether each of the following compounds is optically active or optically inactive: (a) OH H Me OH Me H (b) H Me Cl Et H Me (c) CH3 HO OH H CH3 H (d) (e) H CH2OH OH HO H O H (f) CH2CH3 H CH3 CH3 H H (g) (h)

Organic Chemistry 2
Draw bond-line structures using wedges and dashes for the following compounds: (a) CH3 HO H CH3 H OH H OH (b) Et HO H Me H OH H OH (c) Et HO H H OH Me HO H (d) H Me Cl Me HO H (e) Cl Me H Me HO H

Organic Chemistry 2
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?

Organic Chemistry 2
Draw a Fischer projection for each of the following compounds, placing the !CO2H group at the top: (a) OH O HO OH OH (b) OH OH O OH HO OH (c) OH OH O OH HO OH

Organic Chemistry 2
For each of the following pairs of compounds, determine the relationship between the two compounds: (a) Et H Me H H Me (b)

Organic Chemistry 2
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 chi

Organic Chemistry 2
Based on your analysis in the previous problem, determine whether the following allene is expected to be chiral: C C C Me Me H Me

Organic Chemistry 2
As mentioned in Problem 5.58, some molecules are chiral even though they lack a chirality center. For example, consider the following two compounds and explain the source of chirality in each case: (a) PPh2 PPh2 (S)-BINAP (b)

Organic Chemistry 2
The following compound is known to be chiral. Draw its enantiomer and explain the source of chirality. CH3 H H3C

Organic Chemistry 2
The following compound is optically inactive. Explain why. O O H3C CH3

Organic Chemistry 2
The following compound, whose central ring is referred to as a 1,2,4-trioxane, is an anticancer agent that demonstrates activity against canine osteosarcoma (J. Am. Chem. Soc. 2012, 134, 1355413557). Assign the configuration of each chirality center and then draw all possible stereoisomers of this co

Organic Chemistry 2
Coibacin B is a natural product that exhibits potent anti-inflammatory activity and potential activity in the treatment of leishmaniasis, a disease caused by certain parasites (Org. Lett. 2012, 14, 38783881): O O H H H (a) Assign the configuration of each chirality center in coibacin B. (b) Identify

Organic Chemistry 2
Chiral catalysts can be designed to favor the formation of a single enantiomer in reactions where a new chirality center is formed. Recently, a novel type of chiral copper catalyst was developed that is redox reconfigurable in that the S enantiomer of the product predominates when the CuI form of the

Organic Chemistry 2
In 2010 the structure of the compound (+)-trigonoliimine A (isolated from the leaves of a plant in the Yunnan province of China) was reported as shown below. In 2011, a synthesis of the reported structure was accomplished, and the configuration of a chirality center in the compound was found to have

Organic Chemistry 2
Consider the reaction below, which involves both a dehydrogenation (removal of two neighboring hydrogen atoms) and a Diels-Alder reaction (which we will learn about in Chapter 17). Utilizing a specially designed catalyst, the achiral starting materials are converted to a total of four stereoisomeric

Organic Chemistry 2
When a toluene solution of the sugar-derived compound below is cooled, the molecules self- assemble into fibrous aggregates which work in concert with the surface tension of the solvent to form a stable gel (Langmuir, 2012, 28, 1403914044). Redraw the structure showing both nonaromatic rings in chair

Organic Chemistry 2
A key step of the Wittig reaction (Chapter 20) involves the decomposition of an oxaphosphetane, such as A, into two products (J. Org. Chem. 1986, 51, 33023308). If both chirality centers in A have the R configuration, determine whether the CRC p bond in B will have a cis or trans configuration. A B P

Organic Chemistry 2
Consider the structure of the following ketone (J. Org. Chem. 2001, 66, 20722077): O (a) Does this compound exhibit rotational symmetry? (b) Does this compound exhibit reflectional symmetry? (c) Is the compound chiral? If so, draw its enantiomer.

Organic Chemistry 2
The natural product meloscine can be prepared via a 19-step synthesis, featuring the following allene (see Problems 5.58 and 5.59) as a key intermediate (Org. Lett. 2012, 14, 934937): C C C OSi(iPr)3 N N N Br O O O @ ! (a) Draw a Newman projection of the allene when viewed from the left side of the C

Organic Chemistry 2
Each of 10 stereoisomeric sugar derivatives can be prepared via a multiple-step synthesis starting from either glucuronolactone 1D or its enantiomer 1L. Depending on the specific series of reactions used, the configuration at carbons 2, 3, and 5 can be selectively retained or inverted over the course