Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 5, Problem 5.35P
(a)
Interpretation Introduction
Interpretation:
The type of isomers in limonene has to be identified.
Concept Introduction:
Chiral carbon: A carbon is said to be chiral carbon if it is bonded to four different substituents.
Chirality: It refers to a Carbon atom in a molecule that contains four different substituents.
Enantiomers: They are chiral molecules whose mirror images are not superimposable.
(b)
Interpretation Introduction
Interpretation:
Possibility of having E, Z isomers in limonene has to be identified.
Concept Introduction:
Geometric isomers: Two compounds are considered as geometric isomers of each other if both contain same number of atoms but different in their arrangement.
E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the double bond.
Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the double bond.
(c)
Interpretation Introduction
Interpretation:
Reason for why isomers of limonene smell differently has to be explained.
Concept Introduction:
Chiral carbon: A carbon is said to be chiral carbon if it is bonded to four different substituents.
Chirality: It refers to a Carbon atom in a molecule that contains four different substituents.
Enantiomers: They are chiral molecules whose mirror images are not superimposable.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Draw the structure of the one tertiary (3°) amine with molecular formula C5H13N that does not contain a 3-carbon chain.
You do not have to consider stereochemistry.
You do not have to explicitly draw H atoms
Answer the following questions about compound A, which contains a CH3 group and OH group bonded to the carbon skeleton that consists of three six-membered rings in the conformation shown
a.) Are the CH3 and OH groups oriented cis or trans to each other?b.) Is a substituent on Ca that is cis to the CH3 group located in the axial or equatorial position?
c.) Is an equatorial Br at Cb oriented cis or trans to the OH group?d.) Is the H atom on Cc located cis or trans to the OH group?e.) Is a substituent on Cd that is trans to the OH group located in the axial or equatorial position?
Answer the following questions about compound A, which contains a CH3 group and OH group bonded to the carbon skeleton that consists of three six-membered rings in the conformation shown.a.Are the CH3 and OH groups oriented cis or trans to each other?
b. Is a substituent on Ca that is cis to the CH3 group located in the axial
or equatorial position?
c. Is an equatorial Br at Cb oriented cis or trans to the OH group?
d. Is the H atom on Cc located cis or trans to the OH group?
e.Is a substituent on Cd that is trans to the OH group located in the axial or equatorial position?
Chapter 5 Solutions
Organic Chemistry
Ch. 5.1 - Calculate the index of hydrogen deficiency for...Ch. 5.1 - Prob. 5.2PCh. 5.2 - Write the IUPAC name of each alkene. (a) (b)Ch. 5.2 - Prob. 5.4PCh. 5.2 - Prob. 5.5PCh. 5.2 - Prob. 5.6PCh. 5.2 - Prob. 5.7PCh. 5.2 - Prob. 5.8PCh. 5 - Predict all approximate bond angles about each...Ch. 5 - Prob. 5.10P
Ch. 5 - The structure of 1,2-propadiene (allene) is shown...Ch. 5 - Prob. 5.12PCh. 5 - Draw structural formulas for these alkenes. (a)...Ch. 5 - Name these alkenes and cycloalkenes.Ch. 5 - Prob. 5.15PCh. 5 - Prob. 5.16PCh. 5 - Prob. 5.17PCh. 5 - For each molecule that shows cis, trans isomerism,...Ch. 5 - -Ocimene, a triene found in the fragrance of...Ch. 5 - Prob. 5.20PCh. 5 - Prob. 5.21PCh. 5 - Prob. 5.22PCh. 5 - Prob. 5.23PCh. 5 - Prob. 5.24PCh. 5 - Measure the CH3,CH3 distance in the...Ch. 5 - Prob. 5.26PCh. 5 - Measure the CCC and CCH bond angles in the...Ch. 5 - Prob. 5.28PCh. 5 - Prob. 5.29PCh. 5 - Prob. 5.30PCh. 5 - Prob. 5.31PCh. 5 - Prob. 5.32PCh. 5 - Prob. 5.33PCh. 5 - Pyrethrin II and pyrethrosin are two natural...Ch. 5 - Prob. 5.35PCh. 5 - Prob. 5.36PCh. 5 - Bromine adds to cis- and trans-2-butene to give...
Knowledge Booster
Similar questions
- As mentioned in Problem 3-53, the statin drugs, such as simvastatin (Zocor), pravastatin (Pravachol), and atorvastatin (Lipitor) are the most widely prescribed drugs in the world. (a) Are the two indicated bonds on simvastatin cis or trans? (b) What are the cis/trans relationships among the three indicated bonds on pravastatin? (c) Why cant the three indicated bonds on atorvastatin be identified as cis or trans?arrow_forwardWhich structure has the greatest number of pi electrons?A, Structure 1B. Structure 3C. Structure 4D. Structure 5 Which molecule has the lowest resonance stability?A. Structure 1B. Structure 2C. Structure 3D. Structure 4. Which molecule has the least ability to form hydrogen bonds with water?A. Structure 1B. Structure 2C. Structure 4D. Structure 5 Which aromatic molecules acts as both hydrogen bond donor and hydrogen bondacceptor?A. Structures 1, 2 and 3B. Structures 2, 4 and 5C. Structures 1, 3 and 4D. Structures 3, 4 and 5 Which among the five aromatic molecules will have the least ability to undergo molecularstacking?A. Structure 1B. Structure 2C. Structure 3D. Structure Which aromatic structures contains functional groups which are electron-withdrawing?A. Structures 1, 2 and 4B. Structures 2, 3 and 5C. Structures 2, 4, and 5D. Structures 1, 3, and 4 Which aromatic structures contain functional groups which are electron-donating?A. Structures 1 and 3B. Structures 1 and 4C. Structures…arrow_forwardDraw tartaric acid - 2,3-Dihydroxybutanedioic acid (-dioic means two carboxylgroups), how many stereo isomers will this molecule have? How many of these isomers will be chiral?arrow_forward
- Briefly, but clearly, explain why the –OH hydrogen in acetic acid (CH3CO2H) is more acidic than in ethanol (C2H5OH).arrow_forwardWhat is the relationship of the following two compounds?arrow_forwardPropanal, an aldehyde with the formula CH3CH2CHO, and n-propylamine have identical molecular weights (59 amu) and identical boiling points (49 C) Which molecule do you expect to be more polar and why?arrow_forward
- Answer the following questions for the aromatic compound. 1. is every compound cyclic? yes or no 2. is every compound conjugated? yes or no 3. is every atom with a p-orbital connected to atoms on both sides that have a p-orbital? yes or no 4. Are all p-orbitals in the same plane? yes or noarrow_forwardDraw the structure of the two tertiary (3°) amines with molecular formula C6H15N that contain a group with 3 carbon atoms in the largest group. You do not have to consider stereochemistry. You do not have to explicitly draw H atoms.arrow_forwardChoose one answer for the following. Refer to the diagram below. 1. Hybridization of atom labelled A (sp, sp2, or sp3) 2. Hybridization of atom labelled B (sp, sp2, or sp3) 3. Hybridization of atom labelled C (sp, sp2, sp3) 4.Class compound for functional group D (phenols, aryl halide, alcohols, aromatics, or carboxylic acids) 5. Class compound for functional group E (phenols, aryl halide, alcohols, aromatics, or carboxylic acids)arrow_forward
- The shrub ma huang (Section 5.4A) contains two biologically active stereoisomers—ephedrine and pseudoephedrine—with two stereogenic centers as shown in the given structure. Ephedrine is one component of a once-popular combination drug used by body builders to increase energy and alertness, whereas pseudoephedrine is a nasal decongestant. a.Draw the structure of naturally occurring (−)-ephedrine, which has the 1R,2S configuration. b.Draw the structure of naturally occurring (+)-pseudoephedrine, which has the 1S,2S configuration. c.How are ephedrine and pseudoephedrine related? d.Draw all other stereoisomers of (−)-ephedrine and (+)pseudoephedrine, and give the R,S designation for all stereogenic centers. e.How is each compound drawn in part (d) related to (−)-ephedrine?arrow_forward1,4-Pentadiene (CH2=CH-CH2-CH=CH2) is a liquid at room temperature and has a density of 0.66 g/mL and molar mass of 68.12 g/mol. In a laboratory experiment, 3.80 mL of this compound was treated with 4.80 mL of conc. H2SO4 (100% w/w; molar mass 98.08 g/mol). Note that the density of conc. H2SO4 is 1.84 g/mL. The resulting sulfate ester was then treated with 1.20 mL of water (molar mass 18.02 g/mol) affording, after work- up, 2,4-pentanediol (molar mass 104.15 g/mol) as the crude product. The crude product was then purified by simple distillation, which yielded 2.00 g of pure product. What is the theoretical yield of 2,4-pentanediol expressed in grams? Show calculations. What is the percentage yield of pure 2,4-pentanediol?arrow_forward1,4-Pentadiene (CH2=CH-CH2-CH=CH2) is a liquid at room temperature and has a density of 0.66 g/mL and molar mass of 68.12 g/mol. In a laboratory experiment, 3.80 mL of this compound was treated with 4.80 mL of conc. H2SO4 (100% w/w; molar mass 98.08 g/mol). Note that the density of conc. H2SO4 is 1.84 g/mL. The resulting sulfate ester was then treated with 1.20 mL of water (molar mass 18.02 g/mol) affording, after work- up, 2,4-pentanediol (molar mass 104.15 g/mol) as the crude product. The crude product was then purified by simple distillation, which yielded 2.00 g of pure product. a. Provide a balanced chemical equation to show the reaction between 1,4-pentadiene and sulfuric acid. Do not use molecular formulas in the chemical equation except for sulfuric acid. b. What reactant is the limiting reagent in this chemical equation? Show calculations to support your answer.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning