Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 14, Problem 64P
Interpretation Introduction
Interpretation: The mechanism for the acid-catalyzed dehydration of
Concept introduction: The removal of two substituents from a molecule either in one step or in two steps is called an elimination reaction.
In elimination reaction, abstraction of proton occurs to form an alkene. Elimination reactions are of two types that is
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draw the two possible carbocations that can form when this alkene reacts with a strong acid (such as HBr or H3O+). of the two structures you drew, circle the more stable carbocation
3 Give the systematic name of the given alkene based on its semi-structural formula.
CH,
CH,
CH3
CH,
- C = CH
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-
CH,
CH
-
-
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CH,
Systematic name:
Draw the organic product(s) formed upon the addition of HBr to (a) 2-methyl-2-pentene, (b) trans-2-hexene, and (c) 4-methylcyclohexene. How many regioisomers can be formed in each case?
Chapter 14 Solutions
Organic Chemistry (6th Edition)
Ch. 14.1 - Prob. 2PCh. 14.2 - Problem 16.3 Draw a second resonance structure for...Ch. 14.2 - Prob. 4PCh. 14.2 - Problem 16.5 Farnesyl diphosphate is synthesized...Ch. 14.3 - Prob. 6PCh. 14.4 - Prob. 7PCh. 14.4 - Prob. 8PCh. 14.8 - Problem 16.12 Using hybridization, predict how the...Ch. 14.8 - Problem 16.13 Use resonance theory to explain why...Ch. 14.9 - Prob. 15P
Ch. 14.9 - Prob. 16PCh. 14.10 - Problem 16.17 Draw a stepwise mechanism for the...Ch. 14.11 - Prob. 19PCh. 14.12 - Problem 16.19 Draw the product formed when each...Ch. 14 - Prob. 32PCh. 14 - 16.31 Which of the following systems are...Ch. 14 - 16.32 Draw all reasonable resonance structures for...Ch. 14 - Prob. 35PCh. 14 - 16.35 Explain why the cyclopentadienide anion A...Ch. 14 - Prob. 38PCh. 14 - 16.37 Draw the structure of each compound.
a. in...Ch. 14 - 16.41 Draw the products formed when each compound...Ch. 14 - Prob. 44PCh. 14 - 16.43 Treatment of alkenes A and B with gives the...Ch. 14 - 16.44 Draw a stepwise mechanism for the following...Ch. 14 - Prob. 47PCh. 14 - 16.57 A transannular Diels–Alder reaction is an...Ch. 14 - Draw a stepwise mechanism for the following...Ch. 14 - Prob. 62PCh. 14 - Prob. 63PCh. 14 - Prob. 64PCh. 14 - Prob. 65PCh. 14 - 16.65 The treatment of isoprene with one...
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- ║? What is the structure of the alkene that would produce CH3─ C─ CH2CH3 and H─C─H when treated with ozone and then with zinc and acetic acid? ║ Oarrow_forwardDraw a structural formula for 2-methylpropene. You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. CH4 Sn [1 ? ChemDoodlearrow_forwardHow could 2,6-dimethylheptane be prepared from an alkyne and an alkyl halide? (The prime in R′ signifies that R and R′ can be different alkyl groups.)arrow_forward
- 4-Chlorobut-1-ene is the name of which among the following alkenes? O CH2CI-CH2=CH-CH2 O CH2CI-CH2-CH-CH2 O CH2CI=CH2-CH=CH2 O CH2CI-CH2-CH=CH2arrow_forward1,4-Pentadiene (CH2=CH-CH2-CH=CH2) is a liquid at room temperature and has a density of 0.66 g/mL and molar mass of 68.12 g/mol. In a laboratory experiment, 3.80 mL of this compound was treated with 4.80 mL of conc. H2SO4 (100% w/w; molar mass 98.08 g/mol). Note that the density of conc. H2SO4 is 1.84 g/mL. The resulting sulfate ester was then treated with 1.20 mL of water (molar mass 18.02 g/mol) affording, after work- up, 2,4-pentanediol (molar mass 104.15 g/mol) as the crude product. The crude product was then purified by simple distillation, which yielded 2.00 g of pure product. a. Provide a balanced chemical equation to show the reaction between 1,4-pentadiene and sulfuric acid. Do not use molecular formulas in the chemical equation except for sulfuric acid. b. What reactant is the limiting reagent in this chemical equation? Show calculations to support your answer.arrow_forward1,4-Pentadiene (CH2=CH-CH2-CH=CH2) is a liquid at room temperature and has a density of 0.66 g/mL and molar mass of 68.12 g/mol. In a laboratory experiment, 3.80 mL of this compound was treated with 4.80 mL of conc. H2SO4 (100% w/w; molar mass 98.08 g/mol). Note that the density of conc. H2SO4 is 1.84 g/mL. The resulting sulfate ester was then treated with 1.20 mL of water (molar mass 18.02 g/mol) affording, after work- up, 2,4-pentanediol (molar mass 104.15 g/mol) as the crude product. The crude product was then purified by simple distillation, which yielded 2.00 g of pure product. What is the theoretical yield of 2,4-pentanediol expressed in grams? Show calculations. What is the percentage yield of pure 2,4-pentanediol?arrow_forward
- Pyrethrins, such as jasmolin II (shown below), are a group of natural compounds that are synthesized by flowers of the genus Chrysanthemum (known as pyrethrum flowers) to act as insecticides. CH3 CH2=CH-CH. CH-C- -HCS 0-CH, CH,-C H2C- ČH, Which is not a functional group or structural feature in jasmolin II? cycloalkane carboxylic acid ester alkenearrow_forwardName the following compound: CH3 CH;-CH, CH=ċ-CH3 O 2-methylpentene O 2-methyl-2-pentene O 4-methyl-4-pentene O 2-methyl-2-pentynearrow_forwardDetermine the product of the reaction: CH2-0-č-(CH2)1«CH, CH-0-č-(CH2hCH=CH(CH2),CH, + 3 NAOH CH;-0-č-(CH2le(CH2CH=CH)2(CH2),CH, O=O Oarrow_forward
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