Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 3, Problem 75P
How many ethers have molecular formula C5H12O? Draw their structures and give each a systematic name. What are their common names?
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Compounds X and Y have the formula C6H₁2.
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Compounds X and Y have the formula C6H12.
Both X and Y react with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2-methylpentane.
The heat of hydrogenation of X is less than that of Y.
X and Y react with HBr to form a mixture of the same bromoalkanes, and they both undergo hydroboration/oxidation to give a
mixture of the same alcohols.
What is the structure of Y?
• In cases where there is more than one answer, just draw one.
+
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Compounds A and B are isomers of the molecular formula C9H19Br. Both yield the same alkene C in an elimination reaction. Hydrogenation of C yields the product 2,3,3,4 tetramethyl pentane. What are the structures of A, B, and C?
Chapter 3 Solutions
Organic Chemistry
Ch. 3.1 - Name each of the following:Ch. 3.1 - Draw the structure of a compound with molecular...Ch. 3.1 - Draw the structures and name the four...Ch. 3.1 - Prob. 6PCh. 3.1 - Draw the structure for each of the following: a....Ch. 3.1 - Name the following compounds: a. CH3OCH2CH3 b....Ch. 3.2 - Prob. 11PCh. 3.2 - Prob. 12PCh. 3.3 - Prob. 13PCh. 3.3 - Prob. 14P
Ch. 3.3 - Prob. 15PCh. 3.3 - Prob. 16PCh. 3.3 - What is each compounds systematic name?Ch. 3.4 - Give two names for each of the following alkyl...Ch. 3.4 - Prob. 19PCh. 3.5 - a. What is each ethers systematic name? 1....Ch. 3.6 - Draw the structures of a homologous series of...Ch. 3.6 - Give each of the following a systematic name and...Ch. 3.6 - Prob. 23PCh. 3.6 - Prob. 24PCh. 3.7 - Are the following compounds primary, secondary, or...Ch. 3.7 - Prob. 26PCh. 3.7 - Prob. 27PCh. 3.7 - For each of the following, give the systematic...Ch. 3.8 - Predict the approximate size of the following bond...Ch. 3.9 - Prob. 30PCh. 3.9 - Prob. 31PCh. 3.9 - Prob. 32PCh. 3.9 - Rank the following compounds from highest boiling...Ch. 3.9 - Rank the compounds in each set from highest...Ch. 3.9 - Prob. 35PCh. 3.9 - In which solvent would cyclohexane have the lowest...Ch. 3.10 - a. Draw all the staggered and eclipsed conformers...Ch. 3.10 - Prob. 38PCh. 3.10 - Using Newman projections, draw the most stable...Ch. 3.11 - The bond angles in a regular polygon with n sides...Ch. 3.11 - Prob. 41PCh. 3.11 - Prob. 42PCh. 3.12 - Draw 1,2,3,4,5,6-hexachlorocydohexane with a. all...Ch. 3.13 - The chair conformer of fluorocyclohexane is 0.25...Ch. 3.13 - Using the data in Table 3.9, calculate the...Ch. 3.14 - Prob. 46PCh. 3.14 - Which has a higher percentage of the...Ch. 3.14 - For each of the following disubstituted...Ch. 3.14 - a. Calculate the energy difference between the two...Ch. 3 - a. How many hydrogen does an alkene with 17...Ch. 3 - Draw the structure of octane and isooctaneCh. 3 - Draw a condensed structure and a skeletal...Ch. 3 - Prob. 53PCh. 3 - a. What is each compounds systematic name? b. Draw...Ch. 3 - Which of the following represents a cis isomer?Ch. 3 - a. How many primary carbons does each of the...Ch. 3 - Which of the following conformers of isobutyl...Ch. 3 - Draw a skeletal structure for an alkane that has...Ch. 3 - What is each compounds systematic name? a....Ch. 3 - Which bus a. the higher boiling point:...Ch. 3 - a. Draw Newman projections of the two conformers...Ch. 3 - Ansaid and Motrin belong to the group of drugs...Ch. 3 - Prob. 63PCh. 3 - A student was given the structural formulas of...Ch. 3 - Which of the following conformers has the highest...Ch. 3 - Prob. 66PCh. 3 - Prob. 67PCh. 3 - For rotation about the C-3C-4 bond of...Ch. 3 - Prob. 69PCh. 3 - What is each compounds systematic name? a. b. c....Ch. 3 - Prob. 71PCh. 3 - Why are lower molecular weight alcohols more...Ch. 3 - a. Draw a potential energy diagram for rotation...Ch. 3 - For each of the following compound, determine...Ch. 3 - How many ethers have molecular formula C5H12O?...Ch. 3 - Draw the most stable conformer of the following...Ch. 3 - What is each compounds systematic name?Ch. 3 - Calculate the energy difference between the two...Ch. 3 - The most stable from of glucose (blood sugar) is a...Ch. 3 - Prob. 80PCh. 3 - Explain the following: a. 1-Hexanol has a higher...Ch. 3 - One of the chair conformers of cis-...Ch. 3 - Bromine is a larger atom than chlorine, but the...Ch. 3 - Name the following compounds:Ch. 3 - Prob. 85PCh. 3 - Using the data obtained in Problem 85, calculate...
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- Compounds Y and Z both have the formula C₂H18. Both Y and Z react with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2-methyloctane. The heat of hydrogenation of Y is less than that of Z. Y and Z each undergo hydroboration/oxidation to give a primary alcohol (OH attached to a primary carbon). What is the structure of Y? • In cases where there is more than one answer, just draw one. 1998) 0▾ + n [F ChemDoodle aarrow_forwardReaction of butane (CH 3CH 2CH 2CH 3) with Cl 2 in the presence of light forms two different alkyl chlorides that have molecular formula C 4H 9Cl. Draw the structures of both alkyl chlorides.arrow_forwardThere are several aromatic compounds with the formula C8H9Cl. Draw the ones that have a monosubstituted ring.arrow_forward
- 12. Write bond-line structural formulas for (a.) two primary alcohols, (b.) a secondary alcohol, and (c.) a tertiary alcohol-all having the molecular formula CaH100.arrow_forwardWhat functional group distinguishes each of the following hydrocarbon derivatives? a. halohydrocarbons b. alcohols c. ethers d. aldehydes e. ketones f. carboxylic acids g. esters h. amines Give examples of each functional group. What prefix or suffix is used to name each functional group? What are the bond angles in each? Describe the bonding in each functional group. What is the difference between a primary, secondary, and tertiary alcohol? For the functional groups in ah, when is a number required to indicate the position of the functional group? Carboxylic acids are often written as RCOOH. What does COOH indicate and what does R indicate? Aldehydes are sometimes written as RCHO. What does CHO indicate?arrow_forwardWhat are aromatic hydrocarbons? Benzene exhibits resonance. Explain. What are the bond angles in benzene? Give a detailed description of the bonding in benzene. The electrons in benzene are delocalized, while the electrons in simple alkenes and alkynes are localized. Explain the difference.arrow_forward
- There are 17 possible alkene isomers with the formula C6H12. Draw structures of the five isomers in which the longest chain has six carbon atoms, and give the name of each. Are any of these isomers chiral? (There are also eight isomers in which the longest chain has five carbon atoms, and four isomers in which the longest chain has four carbon atoms. How many can you find?)arrow_forwardDraw the structure(s) of all of the branched alkene isomers, C6H12, that contain 2 methyl branches.arrow_forwardDraw Lewis structures for pyridine and its conjugate acid, the pyridinium ion, C5H5NH+. What are the geometries and hybridizations about the nitrogen atoms in pyridine and in the pyridinium ion?arrow_forward
- IV. Compounds A and B are isomers of the molecular formula C9H19Br. Both yield the same alkene Cin an elimination reaction. Hydrogenation of C yields the product 2,3,3,4 tetramethyl pentane. What are the structures of A, B, and C?arrow_forwardThere are two compounds with the formula C3H6, one of which does not have a multiple bond. Draw its structure and explain why it is much less stable than the isomer with the double bond.arrow_forwardCompounds X and Y are stereoisomers having the formula C6H12.Both X and Y react with one molar equivalent of hydrogen in the presence of a palladium catalyst to form hexane, and they each react with HBr to give a single bromoalkane product.Draw structural formulas for both X and Y.arrow_forward
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