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Introduction to General, Organic and Biochemistry
- 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_forwardIt is sometimes necessary to isomerize a cis alkene to a trans alkene in asynthesis, a process that cannot be accomplished in a single step. Usingthe reactions , devise a stepwise method to convert cis-but-2-ene to trans-but-2-ene.arrow_forwardChoose the most appropriate systematic (IUPAC) name from the choices below that accurately describes the following structure (drawn in a Newman projection). H H. CH3 H;C 3-methyl-4-flouro-1-pentene 4-fluoro-3-methyl-1-pentene 3-methyl-1-alkenyl-4-fluoride 2-fluoro-3-methyl-4-pentene O 4-fluoro-2,3-dimethyl-1-butenearrow_forward
- 11) a) How many different molecules containing one double bond can be used to synthesize 4-methyl-4-heptanol (as the major product) via acid catalyzed hydration with H2SOe and H20? Draw them all below. b) Are any of the structures in part (a) trisubstituted alkenes? If so, redraw it/them below. c) Label (if possible) the structure(s) in part (b) as either Z or E double bond isomers. Bonus Question: ) Recently, the Gademann research group from the University of Zurich, completed the synthesis of (+)-Peyssonnosol, a complex natural product (shown below on the left) which contains seven stereocenters. Briefly describe what the "(t)" symbol in front of the synthesized natural product name means. Me., Me, Me Me HO. Me Me Synthesized ()-Peyssonnosol Starting Materials Used inSynthesisarrow_forward6) Provide the major organic product of the following. x 1. Mg, Et₂0 2. CO₂ 3. H₂O* CH₂CH₂ CH₂ O=O Br OCH₂CH3 1. 2 CH₂MgCl 2. H₂O, H* .H 1. CH₂CH₂C=C 2. H₂O, H* ~arrow_forward18:44 1 Reset Question 4 of 12 CI Provide the correct IUPAC name for the skeletal (line-bond) structure shown here. Stereochemistry is ignored. 5Gº CI Submit 2- 1,2-3,4- 1,1- 2,2- 1- tert- di tri cyclo sec- iso meth carbo) prop bromo) chloroeth ane yl ene yne Tap here or pull up for additional resourcesarrow_forward
- Draw the organic products formed when cyclopentene is treated with each reagent. With some reagents, no reactionoccurs.a. H2 + Pd-Cb. H2 + Lindlar catalystc. Na, NH3d. CH3CO3He. [1] CH3CO3H; [2] H2O, HO–f. [1] OsO4 + NMO; [2] NaHSO3, H2Og. KMnO4, H2O, HO–h. [1] LiAlH4; [2] H2Oi. [1] O3; [2] CH3SCH3j. (CH3)3COOH, Ti[OCH(CH3)2]4, (–)-DETk. mCPBAl. Product in (k); then [1] LiAlH4; [2] H2Oarrow_forwardAlkenes can be hydrated via the addition of borane to yield alcohols with non-Markovnikov regiochemistry. The boron atom is an electrophile and thus follows Markovnikov's rule in adding to the carbon containing the most hydrogens. Oxidation of the alkylborane with basic peroxide yields the product alcohol. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions OR OR RO—B—Ӧн RO-B ÖR OR OHarrow_forward(a) 2-methyl-2-pentanol Draw the structure of the alkene that was used to prepare the alcohol in highest yield. ? ChemDoodle Which process does this employ? 1. Hg(OAc)2, H₂O; 2. NaBH4 1. BH3; 2. H₂O2, NaOH OsO4, H₂O2 √ [Farrow_forward
- (a) 2-methyl-2-pentanol Draw the structure of the alkene that was used to prepare the alcohol in highest yield. 8 ? ChemDoodleⓇ Which process does this employ? 1. Hg(OAc)2, H₂O; 2. NaBH4 1. BH3; 2. H₂O2, NaOH OsO4, H₂O2 #[ ] در Onarrow_forward1. Hydroxylation of €-2-pentene with osmium tetroxide yields a different product than the same reaction using the Z configuration. Draw the structures of the alkenes and show the stereochemistry for each product. Explain any differences between them. 2. Provide the structure of the hydrocarbon that absorbs four molar equivalents of molecular hydrogen on catalytic reduction over a palladium catalyst and yields only butanedial upon ozonolysis using O; followed by treatment with Zn and ACOH.arrow_forwardAn alkene G (C6H12) reacts with cold basic KMnO4 to produce H (C6H14O2). Hydrogenation of Gproduces I (C6H14). Ozonolysis of G produces propanone (CH3COCH3) and propanal(CH3CH2CHO).a) Draw the structure of G, H, I.b) State the reagent(s) and condition for ozonolysis reactionarrow_forward
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