Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 12, Problem 12.73P
Interpretation Introduction
Interpretation: Dihydroxylation occurs by syn or anti addition, is to be determined using the given method.
Concept introduction: In presence of peroxide,
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Acid-catalyzed dehydration of 3,3-dimethyl-2-butanol gives three alkenes: 2,3-dimethyl-2-butene, 3,3-dimethyl-1-butene, and 2,3-dimethyl-1-
butene. Draw the structure of the carbocation intermediate leading to the formation of 2,3-dimethyl-2-butene.
• You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
If more than one structure fits the description, draw them all.
Separate structures with + signs from the drop-down menu.
C
P
opy aste
ChemDoodle
>
Acid-catalyzed dehydration of 3,3-dimethyl-2-butanol gives three alkenes: 2,3-dimethyl-2-butene, 3,3-dimethyl-
1-butene, and 2,3-dimethyl-1-butene. Draw the structure of the carbocation intermediate leading to the
formation of 2,3-dimethyl-2-butene.
• You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
• If more than one structure fits the description, draw them all.
• Separate structures with + signs from the drop-down menu.
/
H₂C
CH₂
CH3
CH3
ChemDoodleⓇ
On []
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
Chapter 12 Solutions
Organic Chemistry
Ch. 12 - Prob. 12.1PCh. 12 - Problem 12.2 What alkane is formed when each...Ch. 12 - Prob. 12.3PCh. 12 - Prob. 12.4PCh. 12 - Prob. 12.5PCh. 12 - Prob. 12.6PCh. 12 - Compound Molecular formula before...Ch. 12 - Problem 12.8 Draw the products formed when...Ch. 12 - Prob. 12.9PCh. 12 - Prob. 12.10P
Ch. 12 - Problem 12.11 (a) Draw the structure of a compound...Ch. 12 - Prob. 12.12PCh. 12 - Prob. 12.13PCh. 12 - Problem 12.14 Draw the products of each...Ch. 12 - Prob. 12.15PCh. 12 - Problem 12.16 Draw all stereoisomers formed when...Ch. 12 - Prob. 12.17PCh. 12 - Problem 12.18 Draw the products formed when both...Ch. 12 - Problem 12.19 Draw the products formed when each...Ch. 12 - Prob. 12.20PCh. 12 - Prob. 12.21PCh. 12 - Problem 12.22 Draw the products formed when each...Ch. 12 - Prob. 12.23PCh. 12 - Problem 12.24 Draw the organic products in each of...Ch. 12 - Prob. 12.25PCh. 12 - Prob. 12.26PCh. 12 - Problem 12.27 Draw the products of each Sharpless...Ch. 12 - Prob. 12.28PCh. 12 - 12.29 Draw the products formed when A is treated...Ch. 12 - Prob. 12.30PCh. 12 - 12.31 Devise a synthesis of the following compound...Ch. 12 - Prob. 12.32PCh. 12 - Prob. 12.33PCh. 12 - Prob. 12.34PCh. 12 - Prob. 12.35PCh. 12 - Prob. 12.36PCh. 12 - 12.37 Stearidonic acid (C18H28O2) is an...Ch. 12 - Draw the organic products formed when cyclopentene...Ch. 12 - Draw the organic products formed when allylic...Ch. 12 - Draw the organic products formed in each reaction....Ch. 12 - Prob. 12.41PCh. 12 - Prob. 12.42PCh. 12 - Prob. 12.43PCh. 12 - What alkene is needed to synthesize each 1,2-diol...Ch. 12 - Prob. 12.45PCh. 12 - 12.46 (a)What product is formed in Step [1] of the...Ch. 12 - Draw the products formed after Steps 1 and 2 in...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. 12.50PCh. 12 - Prob. 12.51PCh. 12 - Prob. 12.52PCh. 12 - Prob. 12.53PCh. 12 - 12.54 An unknown compound A of molecular formula ...Ch. 12 - 12.55 DHA is a fatty acid derived from fish oil...Ch. 12 - Prob. 12.56PCh. 12 - 12.57 Draw the product of each asymmetric...Ch. 12 - 12.58 Epoxidation of the following allylic alcohol...Ch. 12 - Prob. 12.59PCh. 12 - 12.60 Identify A in the following reaction...Ch. 12 - Prob. 12.61PCh. 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. 12.64PCh. 12 - Prob. 12.65PCh. 12 - 12.66 Devise a synthesis of each compound from the...Ch. 12 - Prob. 12.67PCh. 12 - Prob. 12.68PCh. 12 - 12.69 Devise a synthesis of each compound from as...Ch. 12 - Prob. 12.70PCh. 12 - Prob. 12.71PCh. 12 - 12.72 Draw a stepwise mechanism for the following...Ch. 12 - Prob. 12.73PCh. 12 - Prob. 12.74PCh. 12 - 12.75 Sharpless epoxidation of allylic alcohol X...
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- C=CH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H-OH HO: Hjö: C=CH c=CH Hö Hg Hgarrow_forwardCCH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Hjö: -CH3 -CH3 H3O*arrow_forwardThe reaction of CH3CH=CH-CH=CH₂ with excess bromine gives chiefly 1,2-dibromopent-3-ene 3,4-dibromopent-1-ene 1,4-dibromopent-3-ene a mixture of the above three compounds none of the above three compoundsarrow_forward
- What are the reagents used to convert 2-butyne to C4H8? What are the products when that C4H8 is mixed with OsO4, and H2O (the formula will be C4H10O2 racemic)? What is the product when C4H8 is mixed with RCO3H, and H2O (the formula will be C4H10O2 meso)?arrow_forwardH3C CH3 H3C NA C→XT Br Br₂ CH₂Cl₂ H3C Electrophilic addition of bromine, Br₂, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH₂Cl₂. CH3 Br In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br CH3 H3C CH3arrow_forward5A In the following reactions, mixtures of alkenes and ethyl ethers are formed. Draw their structures. Explain which is or are likely to be the main product(s) in each reaction. In case of formation of two isomers of alkenes, explain which is formed in greater proportion CH3 ofi H3C- -Br CH3 EtOHarrow_forward
- Questão 10A certain hydrocarbon had the molecular formula C16H26 and contained two triple bonds. Ozonolysis resulted in CH3(CH2)4CO2H and HO2CCH2CH2CO2H as the only products. What is the reasonable structure for this hydrocarbon? Hexadec-6,10-dino undec-1,5-dino Hept-1,5-dino hex-1,5-dino naharrow_forwardCH3 CH3 Br- Br2 .CH3 CH2Cl2 CH3 H3C H3C Br Electrophilic addition of bromine, Brɔ, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl,. In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 CH3 CH3 CH3 H3C H3C :Br: :Br:arrow_forwardAddition of HBr to allene (CH2 = C = CH2) forms 2-bromoprop-1-ene rather than 3-bromoprop-1-ene, even though 3-bromoprop-1-ene is formed from an allylic carbocation. Considering the arrangement of orbitals in the allene reactant, explain this result.arrow_forward
- Addition of HBr to allene (CH2=C=CH2) forms 2-bromoprop-1-ene rather than 3-bromoprop-1-ene, even though 3-bromoprop-1-ene is formed from an allylic carbocation. Considering the arrangement of orbitals in the allene reactant, explain this result.arrow_forwardSelect the reagent that you would use to convert an alkene to a Markovnikov (more substituted) alcohol without possibility of carbocation rearrangement. o H2SO4, H2O OBH3-THF, then H2O2, H2O, NaOH Hg(OAc)2, H2O, then NaBH4 o OsO4, TBHP, H2Oarrow_forwardAn alkene having the molecular formula C5H10 is treated sequentially with ozone (O3) and zinc/acetic acid to give the product/s shown. H3C O CH3CHCH + H. Draw a structural formula for the alkene. You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. In cases where there is more than one answer, just draw one. P opy aste [* Previous Nextarrow_forward
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