Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 7, Problem 55P
Acid-catalyzed dehydration of
a) Write a stepwise mechanism for the formation of
b) What other
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Provide the structures for each compound name given below, including notation
for stereochemistry (i.e., R, S, E, Z, etc.) if necessary.
a) N-ethylheptanamide
b) methyl ethanoate
c) 2,8-dimethyl-5-nonanone
2-bromobutane can be prepared in the lab by using organic chemicals and bromine in inert solvent.
a) Give the initiation step, the two propagation steps and one possible termination step that
are involve in the production of 2-bromopropane with the presence of uv light.
b) Predict the name of the mechanism in (a).
2. Using 1-butyne as the starting material, write the necessary reactions to convert to the indicated
products.
(a)
Butane
(b)
1-Butene
(c)
2,2-Dibromobutane
(d)
2-Pentane
3. Show how 2-butyne can be converted into 2-butene.
4. Using propyne as the starting material, carry out the following reaction sequences to give the
following products.
(a)
2-Butyne
(b)
2-Butene
(c)
2-Bromobutane
(d)
Pentane
Chapter 7 Solutions
Organic Chemistry - Standalone book
Ch. 7.1 - Name each of the following using IUPAC...Ch. 7.1 - Prob. 2PCh. 7.2 - How many carbon atoms are sp2-hybridized in the...Ch. 7.3 - Prob. 4PCh. 7.3 - Are cis-2-hexene and trans-3-hexene stereoisomers?...Ch. 7.4 - Prob. 6PCh. 7.4 - Prob. 7PCh. 7.4 - Give the IUPAC name of each of the compounds in...Ch. 7.5 - Arrange the following in order of increasing...Ch. 7.6 - Prob. 10P
Ch. 7.6 - Standard enthalpies of formation are known for all...Ch. 7.6 - Prob. 12PCh. 7.6 - Despite numerous attempts, the alkene...Ch. 7.6 - Write structural formulas for the six isomeric...Ch. 7.7 - Place a double bond in the carbon skeleton shown...Ch. 7.9 - Identify the alkene obtained on dehydration of...Ch. 7.10 - Prob. 17PCh. 7.11 - Prob. 18PCh. 7.12 - Prob. 19PCh. 7.13 - The alkene mixture obtained on dehydration of...Ch. 7.14 - Write the structures of all the alkenes that can...Ch. 7.14 - Write structural formulas for all the alkenes that...Ch. 7.15 - A study of the hydrolysis behavior of...Ch. 7.15 - Use curved arrows to illustrate the electron flow...Ch. 7.15 - Predict the major product of the reaction shown.Ch. 7.16 - Prob. 26PCh. 7.17 - Prob. 27PCh. 7.18 - Prob. 28PCh. 7.19 - Predict the major organic product of each of the...Ch. 7.19 - A standard method for the synthesis of ethers is...Ch. 7 - Write structural formulas for each of the...Ch. 7 - Prob. 32PCh. 7 - Give an IUPAC name for each of the following...Ch. 7 - A hydrocarbon isolated from fish oil and from...Ch. 7 - Prob. 35PCh. 7 - Prob. 36PCh. 7 - Prob. 37PCh. 7 - Prob. 38PCh. 7 - Choose the more stable alkene in each of the...Ch. 7 - Suggest an explanation for the fact that...Ch. 7 - Prob. 41PCh. 7 - Write structural formulas for all the alkene...Ch. 7 - Prob. 43PCh. 7 - Prob. 44PCh. 7 - Predict the major organic product of each of the...Ch. 7 - Prob. 46PCh. 7 - Prob. 47PCh. 7 - The rate of the reaction In the first order in...Ch. 7 - Prob. 49PCh. 7 - Prob. 50PCh. 7 - You have available 2,2-dimethylcyclopentanol (A)...Ch. 7 - Prob. 52PCh. 7 - Prob. 53PCh. 7 - Prob. 54PCh. 7 - Acid-catalyzed dehydration of...Ch. 7 - The ratio of elimination to substitution is...Ch. 7 - Prob. 57PCh. 7 - Prob. 58DSPCh. 7 - Prob. 59DSPCh. 7 - Prob. 60DSPCh. 7 - Prob. 61DSPCh. 7 - A Mechanistic Preview of Addition Reactions The...Ch. 7 - Prob. 63DSPCh. 7 - Prob. 64DSPCh. 7 - Prob. 65DSP
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- 2. Using 1-butyne as the starting material, write the necessary reactions to convert to the indicated products. (a) Butane (b) 1-Butene (c) 2,2-Dibromobutane (d) 2-Pentane 3. Show how 2-butyne can be converted into 2-butene. 4. Using propyne as the starting material, carry out the following reaction sequences to give the following products. (a) 2-Butyne (b) 2-Butene (c) 2-Bromobutane (d) Pentane 5. How does one convert 1-pentene to 1-pentyne? 1-Bromobutane to 1-butyne?arrow_forward(b) Indicate all possible alkenes are used to produce the following alky halide. Then, write the mechanistic pathway starting with the most stable alkene. Alkenes Br 3-bromo-3-methylhexanearrow_forwardDraw a structural formula of an alkene or alkenes (if more than one) that undergo acid-catalyzed hydration and without rearrangement give 1-methylcyclohexanol as the major product. • 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. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. ● AAVII -85 ? ChemDoodleⓇ Y [Farrow_forward
- Draw a structural formula of an alkene or alkenes (if more than one) that undergo acid-catalyzed hydration and without rearrangement give 1-methylcyclohexanol as the major product. • 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. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. ● VIL ? ChemDoodle Ⓡ Qt Sn [Farrow_forwardSCHAU Instructions: Use a separate sheet of paper when necessary 1. Draw structures, including all necessary conditions for the following reactions: Organic Reactions Part 2 a) the production of cyclobutyl benzoate from its starting compounds. b) the dehydration of 3-bromohexan-1-ol. c) the condensation of 3-pentanoic acid and N-ethylethanamine. 2. Starting with butene, show how you could prepare butanoic acid in three reaction steps. 3. Write a reaction that shows the production of isopropylbenzene (cumene) from benzene and the appropriate isopropyl derivative. 4. Propose a 2-step mechanism to produce the following compound from the appropriate alcohol. d. Alcohol b. What difficulty would you expect to encounter during this synthesis? 5. Complete the following reactions by filling in the blanks with appropriate structures and/or conditions. H₂O H₂C- NHẠCH, OH malom H₂C H₂Oarrow_forwardDraw structural formulas for the alkenes formed by acid-catalyzed dehydration of each alcohol. Where isomeric alkenes are possible, predict which is the major product. Q.) 1-Methylcyclopentanolarrow_forward
- Draw a structural formula of an alkene or alkenes (if more than one) that undergo acid-catalyzed hydration and without rearrangement give 1-methylcyclohexanol as the major product. • You do not have to consider stereochemistry. • You do not have to explicitly draw Hatoms. • If more than one structure fits the description, draw them all. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. ● 8) *9.8 MUIT / ? ChemDoodle [ ] removearrow_forward1. b) Show the MECHANISM for the POLAR addition of molecular chlorine to cyclopentane. c) The reaction of toluene and ethylbenzene was through the alkyl groups, -CH 3 and -CH 2 CH 3, respectively. Why didn’t xylene, which has TWO methyl groups, react with bromine in the time allotted?arrow_forwardBromine reacts with alkenes in methanol according to the equation (see image 1). When this reaction was carried out with 4-tert-butylcyclohexene, only one isomer was formed with the molecular formula C12H23BrO (80% yield) a) Which of the following is the structure more reasonable for this compound? (see image 2) b) Explain your reasoning through a corresponding mechanismarrow_forward
- Starting with acetylene and 1-bromobutane as the only sources of carbon atoms, show how to synthesize the following. Q.) 6-Methyl-5-decanonearrow_forwardMN.23. Propose a synthetic route to perform the following transformations and also explain it in a paragraph (please remember to explain what did you used to do the synthesis and its purpose and/or effect): a) 3-pentanol———>2-ethylbutanoic acid b) isopropanol———> 2-hydroxyl-2-methylpropanoic acidarrow_forwardAlkenes can be hydrated to form alcohols by (1) hydroboration followed by oxidation with alkaline hydrogen peroxide and (2) acid-catalyzed hydration. Compare the product formed from each alkene by sequence (1) with those formed from (2). Q.)1-Methylcyclohexenearrow_forward
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