EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
9th Edition
ISBN: 9780136781776
Author: Wade
Publisher: PEARSON CO
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Textbook Question
Chapter 14, Problem 14.45SP
Show how you would synthesize the following ethers in good yield from the indicated starting materials and any additional reagents needed.
- a. cyclopentyl n-propyl ether from cyclopentanol and propan-1-ol
- b. n-butyl phenyl ether from phenol and butan-1-ol
- c. 2-ethoxyoctane from an octane
- d. 1-methoxydecane from a decene
- e. 1-ethoxy-1-methylcyclohexane from 2-methylcyclohexanol
- f. trans-2,3-epoxyoctane from octan-2-ol
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Students have asked these similar questions
The product of the electrophilic addition of 3-methyl-2-hexene with propanol and
bromine will produce the following major product with the following in it's name:
O a. 2-ethyl ether and 3 bromine
O b. 2-ethyl ether and 4 bromine
O c. 2-ethyl ether and 2 bromine
O d. 3-ethyl ether and pentane
O e. 3-ethyl ether and 2 bromine
Which of the following alkenes will yield 3-bromo-3-methylpentane as the major
product upon addition of HBr?
IV
Ol only
Oll and II only
OiV only
Oll only
OAII of them
Starting with cyclohexanone, show how to prepare these compounds. In addition to the given starting material, use any other organic or inorganic reagents as necessary.
a. Cyclohexanol
b. Cyclohexene
c. cis-1,2-Cyclohexanediol
d. 1-Methylcyclohexanol
e. 1-Methylcyclohexene
f. 1-Phenylcyclohexanol
g. 1-Phenylcyclohexene
h. Cyclohexene oxide
i. trans-1,2-Cyclohexanediol
11. Predict the product when cis-3-methylcyclopentanol is treated with TsCl/pyridine, followed by sodium
bromide.
a.
trans-1-bromo-3-methylcyclopentane
b. cis-1-bromo-3-methylcyclopentane
c. 1-methylcyclopentene
d. 2-methylcyclopentene
e. 3-methylcyclopentene
Chapter 14 Solutions
EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
Ch. 14.2C - Rank the given solvents in decreasing order of...Ch. 14.2D - Prob. 14.2PCh. 14.2D - In the presence of 18-crown-6, potassium...Ch. 14.3B - Give a common name (when possible) and a...Ch. 14.3C - Prob. 14.5PCh. 14.3C - Name the following heterocyclic ethers.Ch. 14.4 - Propose a fragmentation to account for each...Ch. 14.5 - Prob. 14.8PCh. 14.5 - Prob. 14.9PCh. 14.6 - Prob. 14.10P
Ch. 14.7 - Explain why bimolecular condensation is a poor...Ch. 14.7 - Prob. 14.12PCh. 14.7 - Prob. 14.13PCh. 14.8 - Prob. 14.14PCh. 14.8 - Prob. 14.15PCh. 14.8 - Prob. 14.16PCh. 14.10A - Prob. 14.17PCh. 14.10A - Prob. 14.18PCh. 14.10B - Prob. 14.19PCh. 14.11B - Show how you would accomplish the following...Ch. 14.11B - Prob. 14.21PCh. 14.12 - Prob. 14.22PCh. 14.12 - Prob. 14.23PCh. 14.12 - Prob. 14.24PCh. 14.13 - Prob. 14.25PCh. 14.13 - Prob. 14.26PCh. 14.14 - Prob. 14.27PCh. 14.15 - Give the expected products of the following...Ch. 14 - Write structural formulas for the following...Ch. 14 - Give common names for the following compounds. a....Ch. 14 - Give IUPAC names for the following compounds. a....Ch. 14 - Glycerol (propane-1,2,3-triol) is a viscous syrup...Ch. 14 - Prob. 14.33SPCh. 14 - Show how you would make the following ethers,...Ch. 14 - (A true story.) An inexperienced graduate student...Ch. 14 - Prob. 14.36SPCh. 14 - a. Show how you would synthesize the pure (R)...Ch. 14 - a. Predict the values of m/z and the structures of...Ch. 14 - The following reaction resembles the...Ch. 14 - Prob. 14.40SPCh. 14 - Prob. 14.41SPCh. 14 - Prob. 14.42SPCh. 14 - Give the structures of the intermediates...Ch. 14 - Prob. 14.44SPCh. 14 - Show how you would synthesize the following ethers...Ch. 14 - Prob. 14.46SPCh. 14 - Prob. 14.47SPCh. 14 - Prob. 14.48SPCh. 14 - An acid-catalyzed reaction was carried out using...Ch. 14 - Propylene oxide is a chiral molecule. Hydrolysis...Ch. 14 - Prob. 14.51SPCh. 14 - Prob. 14.52SPCh. 14 - Prob. 14.53SPCh. 14 - Prob. 14.54SPCh. 14 - In 2012, a group led by Professor Masayuki Satake...
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- The product of the electrophilic addition of 3-methyl-2-hexene with propanol and bromine will produce the following major product with the following in it's name: O a. 3-ethyl ether and 2 bromine O b. 2-ethyl ether and 3 bromine O c. 2-ethyl ether and 2 bromine O d. 3-ethyl ether and pentane O e. 2-ethyl ether and 4 brominearrow_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. r Alcohol Starting Materials 1. methanol 2. ethanol 3. 1-propanol 4. 2-propanol 5. cyclohexanol Reagents available a. LiAlH₁ f. PBr3 b. H₂SO4 c. HCI d. HBr i. CH3 MgBr; then H3O+ e. SOC1₂ j. CH3 CH₂ MgBr; then H3O+ g. CrO3, H₂ SO4, H₂O h. NaH k. CH3 CH₂ CH₂ MgBr; then H3O+ I. C6H5 MgBr (phenylmagnesium bromide); then H3O+ m. (CH3)2 CHMgBr: then H3O+t n. Dess-Martin periodinane (DMP) Write the number/letters of the alchol/reagents in the boxes below. Alcohol starting material Reagent for step 1 Reagent for step 2 Reagent for step 3arrow_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. OH Alcohol Starting Materials 1. methanol 2. ethanol 3. 1-propanol 4. 2-propanol 5. cyclohexanol a. LiAlH4 f. PBr3 b. H₂SO4 c. HCI d. HBr e. SOC1₂ Reagents available g. CrO3, H₂SO4, H₂O h. NaH i. CH3 MgBr; then H3O+ j. CH3 CH₂ MgBr; then H3O+ k. CH3 CH₂ CH₂ MgBr; then H3O+ I. C6H5 MgBr (phenylmagnesium bromide); then H3O+ m. (CH3)2 CHMgBr: then H3O+ n. Dess-Martin periodinane (DMP) Write the number/letters of the alchol/reagents in the boxes below. Alcohol starting material 4 Reagent for step 1 n Reagent for step 2 j Reagent for step 3 carrow_forward
- Specify 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. ů Alcohol Starting Materials 1. methanol 2. ethanol 3. 1-propanol 4. 2-propanol 5. cyclohexanol a. LiAlH4 f. PBr3 b. H₂SO4 c. HCI d. HBr e. SOC12 g. CrO3, H₂SO4, H₂O h. NaH Reagents available i. CH3 MgBr; then H3O+ j. CH3 CH₂ MgBr; then H3O+ k. CH3 CH₂ CH₂ MgBr; then H30+ I. C6H5 Mg Br (phenylmagnesium bromide); then H3O+ m. (CH3)2 CHMgBr: then H3O+ n. Dess-Martin periodinane (DMP) Write the number/letters of the alchol/reagents in the boxes below. Alcohol starting material | Reagent for step 1 Reagent for step 2 Reagent for step 3arrow_forwardThese reagents can produce ketones with alkynes A. BH3, THF, H2O2 B. KMnO4 C. O3 D. H2SO4, H2O, HgSO4arrow_forwardcis-Cyclohexane-1,2-diol can be synthesized from cyclohexene by using which reagent? a.O3 b.OsO4 c.H2SO4 d.mCPBAarrow_forward
- 5. Show how the following alcohol can be synthesized. a) 2-methyl butanol from suitable Grignard reagent b) cyclohexanol from chlorocyclohexane c) cylopentanol from cyclopentenearrow_forwardWrite the number/letters of the alchol/reagents in the boxes below. Alcohol starting material Reagent for step 1 Reagent for step 2 Reagent for step 3arrow_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_forward
- Specify 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 f. PBr3 b. H₂SO4 c. HCI d. HBr e. SOCI₂ g. CrO3, H₂ SO4, H₂O h. NaH Reagents available i. CH3 MgBr; then H3O+ j. CH3 CH₂ MgBr; then H3O+ k. CH3 CH₂ CH₂MgBr; then H3O+ I. C6H5 MgBr (phenylmagnesium bromide); then H3O+ m. (CH3)2 CHMgBr: then H3O+ n. Dess-Martin periodinane (DMP) Write the number/letters of the alchol/reagents in the boxes below. Alcohol starting material Reagent for step 1 Reagent for step 2 Reagent for step 3arrow_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. OH Alcohol Starting Materials 1. methanol 2. ethanol 3. 1-propanol 4. 2-propanol 5. cyclohexanol Reagents available a. LiAlH4 f. PBr3 k. CH3 CH₂ CH₂ MgBr; then H3O+ b. H₂SO4 9. CrO3, H₂SO4, H₂O I. CGH, MgBr (phenylmagnesium bromide); then H3O+ c. HC1 h. NaH m. (CH3)2 CHMgBr: then H₂O+ d. HBr i. CH, MgBr; then H3O+ n. Dess-Martin periodinane (DMP) e. SOCI₂ j. CH3 CH₂ MgBr; then H3O+ Write the number/letters of the alchol/reagents in the boxes below. Alcohol starting material Reagent for step 1 Reagent for step 2 Reagent for step 3arrow_forward1. The alkene mixture obtained on dehydration of 2,2-dimethylcyclohexanol contains a significant amount of 1,2-dimethylcyclohexene a. Draw the structure of 1,2-dimethylcyclohexene b. Show a mechanism for the formation of this alkene product c. Draw the structures and give the names of any other alkene products, explaining how they could arise from the dehydration reactionarrow_forward
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