Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 12, Problem 59P
It is sometimes necessary to isomerize a cis
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It is sometimes necessary to isomerize a cis alkene to a trans alkene in a synthesis, a process that cannot be accomplished in a single step. Using the reactions you have learned in Chapters 8–12, devise a stepwise method to convert cis-but-2-ene to trans-but-2-ene.
4) For the following reaction map, provide the products, or reagents/
direction of the reaction arrow!
MeO
OMe
MeO
OH
4. What are the products obtained from the following elimination reaction? Indicate the major
product.
CH;CH2CCH3
H2O
CI
5. a) Determine the major product that is formed when the alkyl halide reacts with a hydroxide ion in
an elimination reaction.
CH;CH,CH,CH,CCH3
Br
b) For the major elimination product obtained in 5a), which stereoisomer (cis or trans) is obtained in
greater yield? Draw the two isomers and provide the names of the compounds.
Chapter 12 Solutions
Organic Chemistry (6th Edition)
Ch. 12.1 - Prob. 1PCh. 12.3 - Problem 12.2 What alkane is formed when each...Ch. 12.3 - Prob. 3PCh. 12.3 - Prob. 4PCh. 12.3 - Prob. 5PCh. 12.3 - Prob. 6PCh. 12.3 - Compound Molecular formula before...Ch. 12.4 - Problem 12.8 Draw the products formed when...Ch. 12.5 - Prob. 9PCh. 12.5 - Prob. 10P
Ch. 12.5 - Problem 12.11 (a) Draw the structure of a compound...Ch. 12.5 - Prob. 12PCh. 12.5 - Prob. 13PCh. 12.6 - Problem 12.14 Draw the products of each...Ch. 12.8 - Prob. 15PCh. 12.8 - Problem 12.16 Draw all stereoisomers formed when...Ch. 12.9 - Prob. 17PCh. 12.9 - Problem 12.18 Draw the products formed when both...Ch. 12.10 - Problem 12.19 Draw the products formed when each...Ch. 12.10 - Prob. 20PCh. 12.10 - Prob. 21PCh. 12.11 - Problem 12.22 Draw the products formed when each...Ch. 12.11 - Prob. 23PCh. 12.12 - Problem 12.24 Draw the organic products in each of...Ch. 12.13 - Prob. 25PCh. 12 - 12.29 Draw the products formed when A is treated...Ch. 12 - Prob. 30PCh. 12 - Prob. 31PCh. 12 - Prob. 32PCh. 12 - Prob. 33PCh. 12 - Draw the organic products formed when cyclopentene...Ch. 12 - Draw the organic products formed when allylic...Ch. 12 - Prob. 39PCh. 12 - Prob. 40PCh. 12 - Prob. 41PCh. 12 - What alkene is needed to synthesize each 1,2-diol...Ch. 12 - 12.48 Draw the products formed in each oxidative...Ch. 12 - What alkene or alkyne yields each set of products...Ch. 12 - Prob. 47PCh. 12 - Prob. 48PCh. 12 - Prob. 49PCh. 12 - Prob. 50PCh. 12 - 12.57 Draw the product of each asymmetric...Ch. 12 - 12.60 Identify A in the following reaction...Ch. 12 - Prob. 58PCh. 12 - 12.62 It is sometimes necessary to isomerize a cis...Ch. 12 - 12.63 Devise a synthesis of each compound from...Ch. 12 - Prob. 61P
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- As a rule, axial alcohols oxidize somewhat faster than equatorial alcohols. Which would you expect to oxidize faster, cis-4-tert-butylcyclo-hexanol or trans-4-tert-butylcyclohexanol? Draw the more stable chair conformation of each molecule.arrow_forwardAnother 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_forwardDraw the structure for an alkene that gives the following reaction product. 1. Hg(OАc)2, Н2О ? -CHCH3 2. NABH4 ОН Ignore alkene stereochemistry. You do not have to explicitly draw H atoms. In cases where there is more than one answer, just draw one. Visited opy aste ChemDoodlearrow_forward
- Draw the product formed from cyclohex-2-enone in each of three reactions. Reaction 1 Reaction 2 Reaction 1 1. NaCN 1. (CH3)2CuLi Reaction 2 product product 2. H3O*, H20 2. CH3CH21 A 1. EtO,CCH,CO¿Et NaOEt, HOET 2. Hао", Н-0, д Reaction 3 Reaction 3 productarrow_forward3. Provide the mechanism going from a cyclohexenone to an a,ß-unsaturated carbonyl and a ketone. + H-OH RO, ROH, Aarrow_forwardWhich represents an efficient synthetic route to go from an alkane to an alkene? O elimination with NaNH2, followed by a water workup O anti-Markovnikov hydrohalogenation, followed by elimination O radical bromination, followed by elimination O hydration, followed by elimination O hydration, followed by ozonolysis of the double bondarrow_forward
- 4. Give the starting alkene and any other reagents needed to selectively make the following compounds (with no organic byproducts!): OH L Eto OH all OH Br Br Brarrow_forwardWhat reagent/reagents is/are necessary to transform the starting molecule into the desired product? SO3H ?arrow_forwardTreatment of alkenes A and B with HBr gives the same alkyl halide C. Draw a mechanism for each reaction, including all reasonable resonance structures for any intermediate. Br -CHCH2CH, HBr HBr -CH=CHCH, -CH2CH=CH2 A B.arrow_forward
- Draw the product formed from cyclohex-2-enone in each of three reactions. Reaction 1 Reaction 2 Reaction 1 1. NaCN 1. (CH3)2CULI Reaction 2 product product 2. H30*, H2O 2. CH3CH2I 1. EtO,CCH2CO½ET NaOEt, HOET 2. Hао", Н-о, д Reaction 3 Reaction 3 productarrow_forward35) Draw the major product of the following reaction: 1. R₂BH 2. H₂O₂, OH -C=C-Harrow_forward6) 25pts. Draw the structure of the major alkene product (or products) formed by treatment of each of the following haloalkanes with sodium ethoxide in ethanol. Assume the mechanism is E2 elimination. t-BuO K t-BUOH Br CH3 Eto Na F ETOH CH2CH3 CI H- Eto Na -CH2CH3 ELOH H- ČH3 Br Eto Na ELOH CH3 CI, H Eto Na CH2CH3 H3C H D ELOHarrow_forward
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