Concept explainers
a)
Interpretation:
How to carry out the conversion shown is to be stated.
Concept introduction:
Terminal
To state:
How to carry out the conversion shown.
b)
Interpretation:
How to carry out the conversion shown is to be stated.
Concept introduction:
The alkene is converted in to a dibromo derivative by treating with Br2 in the presence of CH2Cl2. The dibromo derivative is then treated with two equivalents of KOH when dehydrohalogenation takes place yield a terminal
To state:
How to carry out the conversion shown.
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Chapter 9 Solutions
Organic Chemistry
- 70. Which reagents best accomplish this transformation? OCH2CH3 a C d. 1. NaBH4, ether 2. H3O 3. CH3(CO)CH3, H (cat.) 1. NaBH4, ether 2. NaOH, heat 3. CH3(CO)CH3, NaOH (cat.) 1. LIAIH4, ether 2. H30* 3. CH3(CO)CH3, H (cat.) 1. LIAIH4, ether 2. NaOH, heat 3. CH3(CO)CH3, NaOH (cat.)arrow_forwardWhich of the following aldehydes has the highest solubility in water? A) CH₃CH₂C(=O)H B) CH₃CH₂CH₂CH₂C(=O)H C) CH₃(CH₂)₅C(=O)H D) CH₃(CH₂)₁₀C(=O)H E) All of these have equal solubility.arrow_forwardChoose reagents to convert 2-cyclohexenone to the following compounds. Syntheses may require several steps. Use letters from the table to list reagents in the order used (first at the left). i 1. Li(CH2=CH)2Cu Reagents a 1. Li(CH3)2Cu 2. H3O+ e 1. Li(C6H5)2Cu 2. H3O+ b 1. NaBH4 f CH2l2/Zn(Cu) / ether j 2. H3O+ C NH3 / KOH g 1. CH3MgBr/dry ether k 2 H3O+ d H2NNH2/KOH h HN(CH3)2 HO CH3 a) b) OH N(CH3)2 2. H3O+ (C6H5)3P+-CH2 H₂ over Pd/C KMnO4/H3O+arrow_forward
- Another important pattern in organic synthesis is the construction of CC bonds. Using your reaction roadmap as a guide, show how to convert propane into hex-1-en-4-yne. You must use propane as the source of all of the carbon atoms in the hex-1-en-4-yne product. Show all reagents needed and all molecules synthesized along the way.arrow_forwardAlcohols undergo an oxidation reaction to yield carbonyl compounds on treatment with CrO3. For example, 2-tert-butylcyclohexanol gives 2-tert-butylcyclohexanone. If axial OH groups are generally more reactive than their equatorial isomers, which do you think reacts faster, the cis isomer of 2-tert-butylcyclohexanol or the trans isomer? Explain.arrow_forwardChoose the reagents that can be used to achieve the following conversion. More than one reaction is required, and reactions from earlier chapters may be necessary. Reagents may be used more than once. CH3-CH2-C-CH3 CH3-CH=CH-CH3 H2SO4 H,SO, 1 2. 180°C 140°C (0) H2 3. 4 Pt H+ H20 5. 6. CH;OH H2SO, (Enter multiple answers as a comma-separated list.)arrow_forward
- Dehydrohalogenation of 1-chloro-1-methylcyclopropane affords two alkenes (A and B) as products. Explain why A is the major product despite the fact that it contains the less substituted double bond.arrow_forwardWhich of the following reactions or series of reactions will lead to the formation of methoxycyclohexane? OH CH₂OH/A 1. CH3MgBr/ ether 2. H*/H₂O 1. Na 2. CH₂CH₂I 1. Hg(OAc)2/ CH₂OH 2. NaBH4 1. MCPBA 2. H¹/ CH₂OHarrow_forwardCH3 OCH2CH2CH CH3 (10) (11) alkyl bromide/ phenyl bromide sodium alkoxide/ sodium phenoxidearrow_forward
- Fill in the missing product/reagentsarrow_forwardChlordane, like DDT, is an alkyl halide that was used as an insecticide for crops such as corn and citrus and for lawns. In 1983, it was banned for all uses except against termites, and in 1988, it was banned for use against termites as well. Chlordane can be synthesized from two reactants in one step. One of the reactants is hexachlorocyclopentadiene. What is the other reactant?arrow_forwardWhat conditions could be used to carry out the transformation shown below? More than one step may be required 1 AICH 2. H₂, PtO₂ t OH AICI 1 AC 2 H₂ Pd/c CI Matr or borarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning