Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 5, Problem 42P
(a) Assuming that the rate-determining elementary step in the reaction of
b) Two stereoisomers of
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1) The carbon-oxygen double bond present in aldehydes and ketones is very polar. What does this mean and how does it arise?
2) The carbon-oxygen double bond is readily attacked by nucleophiles like cyanide ions or ammonia.
(i) What do you understand by the term nucleophile?
(ii) Which part of the carbon-oxygen double bond is attractive to nucleophiles?
3) Why is there a difference between aldehydes and ketones in their response to oxidizing agents such as potassium dichromate(VI) solution acidified with dilute sulfuric acid?
Consider the reaction of NaCl with 2-
bromo-2-methylhexane in
acetone/water.
Predict the change in rate if the
concentrations of both the 2-bromo-2-
methylhexane and the NaCl are doubled.
A) The reaction rate stays the same.
B) The reaction rate doubles.
C) The reaction rate is halved.
D) The reaction rate quadruples
E) The reaction rate triples.
Acid-catalyzed dehydration of 3,3-dimethyl-2-butanol gives three alkenes: 2,3-dimethyl-2-butene, 3,3-dimethyl-
1-butene, and 2,3-dimethyl-1-butene. Draw the structure of the carbocation intermediate leading to the
formation of 2,3-dimethyl-2-butene.
• You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
• If more than one structure fits the description, draw them all.
• Separate structures with + signs from the drop-down menu.
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H₂C
CH₂
CH3
CH3
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Chapter 5 Solutions
Organic Chemistry - Standalone book
Ch. 5.1 - Prob. 1PCh. 5.1 - Prob. 2PCh. 5.1 - Many compounds contain more than one functional...Ch. 5.2 - Prob. 4PCh. 5.3 - Prob. 5PCh. 5.4 - Classify the isomeric C4H10O alcohols as being...Ch. 5.5 - Bromine is less electronegative than chlorine, yet...Ch. 5.6 - Prob. 8PCh. 5.7 - Prob. 9PCh. 5.8 - Prob. 10P
Ch. 5.8 - Prob. 11PCh. 5.9 - Carbocations are key intermediates in petroleum...Ch. 5.9 - Prob. 13PCh. 5.9 - Prob. 14PCh. 5.11 - Prob. 15PCh. 5.13 - Prob. 16PCh. 5.14 - For the reaction of a primary alcohol RCH2OH with...Ch. 5.15 - Prob. 18PCh. 5 - Write structural formulas for each of the...Ch. 5 - Prob. 20PCh. 5 - Prob. 21PCh. 5 - Write structural formulas for all the...Ch. 5 - Prob. 23PCh. 5 - Prob. 24PCh. 5 - Epichlorohydrin is the common name of an...Ch. 5 - Prob. 26PCh. 5 - Prob. 27PCh. 5 - Prob. 28PCh. 5 - Some of the most important organic compounds in...Ch. 5 - Prob. 30PCh. 5 - Prob. 31PCh. 5 - Prob. 32PCh. 5 - Prob. 33PCh. 5 - Prob. 34PCh. 5 - Prob. 35PCh. 5 - Prob. 36PCh. 5 - Prob. 37PCh. 5 - Prob. 38PCh. 5 - Prob. 39PCh. 5 - Prob. 40PCh. 5 - The reaction of 2,2-dimethyl-1-propanol...Ch. 5 - (a) Assuming that the rate-determining elementary...Ch. 5 - The reaction of 3-tert-butyl-3-pentanol with...Ch. 5 - Prob. 44PCh. 5 - Prob. 45PCh. 5 - Prob. 46DSPCh. 5 - Prob. 47DSPCh. 5 - Prob. 48DSPCh. 5 - Prob. 49DSPCh. 5 - Prob. 50DSPCh. 5 - Prob. 51DSPCh. 5 - Prob. 52DSP
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- Acid-catalyzed dehydration of 3,3-dimethyl-2-butanol gives three alkenes: 2,3-dimethyl-2-butene, 3,3-dimethyl-1-butene, and 2,3-dimethyl-1- butene. Draw the structure of the carbocation intermediate leading to the formation of 2,3-dimethyl-2-butene. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. If more than one structure fits the description, draw them all. Separate structures with + signs from the drop-down menu. C P opy aste ChemDoodle >arrow_forwardAcid-catalyzed dehydration of 3-methyl-2-pentanol gives three alkenes: 3-methyl-1-pentene, 3-methyl-2-pentene, and 3-methylenepentane. Draw the structure of the carbocation intermediate leading to the formation of 3-methyl-2-pentene.arrow_forwardExplain why pentane-2,4-dione forms two alkylation products (A and B) when the number ofequivalents of base is increased from one to two.arrow_forward
- In the substitution reaction of 2-chloro-2,4- dimethylpentane with water, the rate at which the alcohol product is formed depends on the concentration of the nucleophile. Select one: True Falsearrow_forwardWhen trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone. Why doesn’t the cis isomer yield the oxide?arrow_forwardDetermine the structure of the methyl ester and organomagnesium bromide reagents that can be combined to form the following alcohol: Part 1: Draw the bond-line formula for the methyl ester reagent. Disregard stereochemistry. Part 2: Draw the bond-line formula for the organomagnesium bromide reagent. Disregard stereochemistry.arrow_forward
- 10) For the reaction between isopropyl 1-propyl (or 'n-propyl') ether and HBr, which type of reaction best matches the expected products? A) Acid-catalyzed dehydration B) Nucleophilic substitution reaction C) Ether cleavage reaction D) Nucleophilic addition-elimination reactionarrow_forwardShow how you would use simple chemical tests to distinguish between the following pairs of compounds. In each case, describe what you would do and what you would observe. (a) cyclohexanol and cyclohexene (b) cyclohexanol and cyclohexanone (c) cyclohexanone and 1-methylcyclohexanolarrow_forward3-Chloro-2-methylpropene reacts with sodium methoxide in methanol to form 3-methoxy-2-methylpropene. For each of the following changes in the reaction conditions, state whether the reaction rate would increase, decrease, or remain the same. Explain your reasoning. In some cases the identity of the major organic product would be expected to change; in such cases, give the expected major product. (a) dimethyl sulfoxide (DMSO) is used in place of methanol (b) methanol is used by itself without sodium methoxide (c) 1-chloro-2,2,-dimethylpropane is used in place of 3-chloro-2-methylpropenearrow_forward
- The enamine prepared from acetone and dimethylamine is shown here in its lowest-energy form. (a) What is the geometry and hybridization of the nitrogen atom? (b) What orbital on nitrogen holds the lone pair of electrons? (c) What is the geometric relationship between the p orbitals of the double bond and the nitrogen orbital that holds the lone pair? Why do you think this geometry represents the minimum energy?arrow_forwardWhen trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone –arrow_forwardWhen propene reacts with gaseous hydrogen bromide, HBr, two products, 1-bromopropane and 2-bromopropane are formed. The reaction is a two-step process in which the electrophilic attack occurs in the first step. Identify the electrophile in this reaction Draw a diagram showing the first step of the reaction that leads to the production of 2-bromopropane.arrow_forward
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