ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
9th Edition
ISBN: 9780137249442
Author: Wade
Publisher: INTER PEAR
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Textbook Question
Chapter 9.7A, Problem 9.7P
Show how you might synthesize the following compounds, using acetylene and any suitable
- a. hex-1-yne
- b. hex-2-yne
- c. hex-3-yne
- d. 4-methylhex-2-yne
- e. 5-methylhex-2-yne
- f. cyclodecyne
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11. Predict the product when cis-3-methylcyclopentanol is treated with TsCl/pyridine, followed by sodium
bromide.
a.
trans-1-bromo-3-methylcyclopentane
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c. 1-methylcyclopentene
d. 2-methylcyclopentene
e. 3-methylcyclopentene
1. 2-bromobutane + cyclohexanol + NaH à (major product)
c. 2-butoxycyclohexane
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b. 1-butene
d. no
e. something else!
2. t-butylbromide + sodium ethoxide in ethanol à (major product)
a. 2-methylpropene
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b. t-butyl ethyl ether
c. 1-methylbutene
d. no
e. something else!
3. potassium t-butoxide + 1-bromobutane in t-butyl alcohol room
temperature à (major product)
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reaction
c. 2-methylpropene d. no
b. butyl t-butyl ether
e. something else!
4. t-butyl bromide + boiling hot water à (major product)
a. 2-methylpropene
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e. something else!
5. 2-chloropropane + acetic acid (2 eq) / KOH (1 eq) / DMF à(major
product)
c.
b.
d. no reaction
e. something
а.
HO.
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6.
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d. 1,2-
a. 2-methylpropene
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e. something else!
7. cyclopentanol+ NaH + DMSO + bromopropane à(major product)
a. cyclopentene
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b. propene
e. something else!!
c. propyl cyclopentyl…
Show how to convert propene to each of these compounds, using any inorganic reagents as necessary.
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b.1,2-Propanediol
c. 1-Propanol
d. 2-Propanol
e. Propanal
f. Propanone
g. Propanoic acid
h. l-Bromo-2-propanol
i. 3-Chloropropene
j. 1,2,3-Trichloropropane
k. 1-Chloropropane
l. 2-Chloropropane
m. 2-Propen-1-ol
n. Propenal
Chapter 9 Solutions
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
Ch. 9.1 - a. Count the elements of unsaturation in...Ch. 9.2 - Prob. 9.2PCh. 9.4B - What reaction would acetylene likely undergo if it...Ch. 9.6 - Prob. 9.4PCh. 9.6 - Predict the products of the following acid-base...Ch. 9.7A - Solved Problem9-1 showed the synthesis of...Ch. 9.7A - Show how you might synthesize the following...Ch. 9.7B - Prob. 9.8PCh. 9.7B - Show how you would synthesize...Ch. 9.8 - When 2,2-dibromo-1-phenylpropane is heated...
Ch. 9.8 - When 2,2-dibromo-1-phenylpropane is heated...Ch. 9.9C - Show how you would convert a. oct-3-yne to...Ch. 9.9C - The fragrance of (Z)-1-phenylhex-2-en-1-ol...Ch. 9.9D - In the addition of just 1 mole of bromine to 1...Ch. 9.9E - Propose a mechanism for the entire reaction of...Ch. 9.9E - Predict the major product(s) of the following...Ch. 9.9E - Propose a mechanism for the reaction of pent-1-yne...Ch. 9.9E - Show how hex-1-yne might be converted to a....Ch. 9.9F - When pent-2-yne reacts with mercuric sulfate in...Ch. 9.9F - Prob. 9.20PCh. 9.9F - Prob. 9.21PCh. 9.9F - Prob. 9.22PCh. 9.10A - Predict the product(s) you would expect from...Ch. 9.10B - Prob. 9.24PCh. 9.10B - Prob. 9.25PCh. 9 - Prob. 9.26SPCh. 9 - Give common names for the following compounds. a....Ch. 9 - Prob. 9.28SPCh. 9 - Prob. 9.29SPCh. 9 - Using cyclooctyne as your starting material, show...Ch. 9 - Prob. 9.31SPCh. 9 - Prob. 9.32SPCh. 9 - Predict the products of reaction of pent-1-yne...Ch. 9 - Show how you would accomplish the following...Ch. 9 - Show how you would synthesize the following...Ch. 9 - Predict the products formed when CH3CH2C C : Na+...Ch. 9 - Prob. 9.37SPCh. 9 - Prob. 9.38SPCh. 9 - When compound Z is treated with ozone, followed by...Ch. 9 - Show how you would convert the following starting...Ch. 9 - The following functional-group interchange is a...Ch. 9 - Using any necessary inorganic reagents, show how...Ch. 9 - Prob. 9.43SP
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 1. What alkene will produce the HIGHEST yield of the alkyl halide below? 2. Which of the following alkynes can be deprotonated by NaNH2 in liquid NH3? a. Pent-2-yne b. Hex-3-yne c. none of these d. 3-Methylbutyne e. 3-Methylhex-2-ynearrow_forwardSpecify both the alcohol starting material and the reagents you would use in each step in a synthesis of the compound shown. If the synthesis requires only two steps enter "none" for step 3. Br Alcohol Starting Materials 1. methanol 2. ethanol 3. 1-propanol 4. 2-propanol 5. cyclohexanol a. LiAlH4 b. H₂SO4 c. HCI d. HBr e. SOCI₂ Reagent for step 2 Reagent for step 3 Reagents Available f. PBr3 g. CrO3 h. NaH i. CH3MgBr j. CH3CH₂MgBr k. CH₂CH₂CH₂MgBr I. C6H5MgBr (phenylmagnesium bromide) m. (CH3)2CHMgBr pyridinium chlorochromate (PCC) Write the number/letters of the alchol/reagents in the boxes below. Alcohol starting material Reagent for step 1 Paarrow_forward8. Carry out the following syntheses: a. Cyclopentene to n-propylcyclopentane b. Cyclopentanol to n-propylcyclopentanearrow_forward
- By means of series of equations, outline a method for carrying out the ff. conversions. You may use any reagents you wish. More than one step may be requiredarrow_forwardFill in the missing structure(s) for the reaction pathways shown below. Provide allstarting material(s), reagent(s), or product(s). If more than one product can be formed,draw all major products. If more than one starting material or reagent is possible, writeall starting materials and reagents.arrow_forward2-Methyl-2-butene reacts with HBr in the presence of peroxide to give a. a secondary alkyl bromide. b. a primary alkyl bromide. c. a tertiary alkyl bromide. d. a vicinal dibromide.arrow_forward
- B. Supply the missing reagent, product or starting material of the following reactions. 1. NACN 2. H2SO4, H2O 1. Zn(Hg), H3O* 2. NH-NH>, КОН H. 3. I НО, 4. Reagent I:arrow_forwardIdentify the role/function of the indicated molecule in the reaction? 1. LIAIH, ether 2. Но NaN3 Br -NH2 a. Nucleophile b. Electrophile c. Base O d. Acidarrow_forwardChoose the two alkyl bromides and the hydrogenation method that must be used to synthesize these alkenes from acetylene. Enter your answer as two letters in alphabetical order, followed by a number; i.e. ac2, not ca2. Do not use punctuation. Alkyl Halides a. CH3CH,Br. b. CH3(CH2)4Br c. CH3(CH2);Br d. CH3(CH2)6Br e. CH3(CH2);Br f. CH3(CH2);Br g. CH3(CH2)12B Hydrogenation Method 1. H2, Lindlar's catalyst 2. Na, NH3 (1) Alkene #1: H3C CH3 Alkene #2: CH3 H3Carrow_forward
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