(a)
Interpretation:
The alkene that gives same or different alcohol from either oxymercuration-reduction or hydroboration oxidation is to be stated.
Concept introduction:
Oxymercuration-reduction is one of the methods used to convert
Hydroboration reaction is a two-step reaction, which involves conversion of alkene into alcohol. This type of reaction follows anti-Markovnikov’s rule.
(b)
Interpretation:
The alkene that gives same or different alcohol from either oxymercuration-reduction or hydroboration oxidation is to be stated.
Concept introduction:
Oxymercuration-reduction is one of the methods used to convert alkenes into alcohols. This type of reaction follows Markovnikov’s rule.
Hydroboration reaction is a two-step reaction, which involves conversion of alkene into alcohol. This type of reaction follows anti-Markovnikov’s rule.
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Chapter 5 Solutions
Organic Chemistry
- Give the structure of the product formed when each of the following alkenes reacts with bromine in water: (a) 2-Methyl-1-butene (c) 3-Methyl-1-butene (b) 2-Methyl-2-butene (d) 1-Methylcyclopentenearrow_forwardtrans-3-hexene and cis-3-hexene differ in one of the following ways. Which one? (A) Products of hydrogenation (B) Products of ozonlysis (C) Products of bromine (Br2) addition (D) Products of hydroboration-oxidationarrow_forwardFor each alkane, which mono brominated derivatives could you form in good yield by free-radical bromination?(a) cyclopentane (b) methylcyclopentane(c) 2-methylpentane (d) 2,2,3,3-tetramethylbutanearrow_forward
- Propose a structural formula for the product(s) when each of the following alkenes is treated with H2O/H2SO4. Why are two products formed in part (b), but only one in parts (a) and (c)? (a) 1-Hexene gives one alcohol with a molecular for- mula of C6H14O. (b) 2-Hexene gives two alcohols, each with a molecu- lar formula of C6H14O. (c) 3-Hexene gives one alcohol with a molecular for- mula of C6H14O.arrow_forwardWrite the structure of the major organic product obtained by hydroboration–oxidation of each of the following alkenes: (a) 2-Methylpropene (d) Cyclopentene (b) cis-2-Butene (e) 3-Ethyl-2-pentenearrow_forwardAlkenes can be hydrated to form alcohols by (1) hydroboration followed by oxidation with alkaline hydrogen peroxide and (2) acid-catalyzed hydration. Compare the product formed from each alkene by sequence (1) with those formed from (2). Q.)1-Methylcyclohexenearrow_forward
- Bromine reacts with alkenes in methanol according to the equation: - When this reaction was carried out with 4-tert-butylcyclohexene, only one isomer was formed with the molecular formula C12H23BrO (80% yield). Which of the following is the structure more reasonable for this compound?. Explain your reasoning through acorresponding mechanism.arrow_forwardSome of the following examples can show geometric isomerism, and some cannot. Forthe ones that can, draw all the geometric isomers, and assign complete names using theE-Z system.(a) 3-bromo-2-chloropent-2-ene (b) 3-ethylhexa-2,4-diene(c) 3-bromo-2-methylhex-3-ene (d) penta-1,3-diene(e) 3-ethyl-5-methyloct-3-ene (f) 3,7-dichloroocta-2,5-dienearrow_forward(a) Cyclohexa-1,3-diene can be converted into a tetrasubstituted haloalkane when reacted with bromine in ether. Write a balanced chemical equation for the reaction that occurs and state the expected observation. (b) Compound A and B are alkenes with the same molecular formula C5H10. Compound A is a branched-chain alkene while compound B is a straight-chain alkene. The reaction between compound A with hydrogen bromide produces major product C which is optically active. (i) Draw TWO (2) possible structures for compound B. (ii) Outline the mechanism for the reaction between compound A with hydrogen bromide to form major product C. (iii) Name the product formed when compound A undergoes bromination reaction.arrow_forward
- Disiamylborane adds only once to alkynes by virtue of its two bulky secondary isoamylgroups. Disiamylborane is prepared by the reaction of BH3 # THF with an alkene.(a) Draw the structural formulas of the reagents and the products in the preparation ofdisiamylborane.(b) Explain why the reaction in part (a) goes only as far as the dialkylborane. Why isSia3B not formed?arrow_forwardShow how you might synthesize the following compounds starting with bromobenzene, andalkyl or alkenyl halides of four carbon atoms or fewer.(a) 3-phenylprop-1-ene (b) 5-methylhex-2-ene *(c) dec-5-enearrow_forward1. Deduce the structure of each compound from the information given. All unknowns in this problem have molecular formula C8H12. (a) Upon catalytic hydrogenation, unknown W gives cyclooctane. Ozonolysis of W, followed by reduction with dimethylsulfide, gives octanedioic acid, HOOC—(CH2)6—COOH. Draw the structure of W. (b) Upon catalytic hydrogenation, unknown X gives cyclooctane. Ozonolysis of X, followed by reduction with dimethyl sulfide, gives two equivalents of butanedial, O=CH—CH2CH2—CH=O. Draw the structure of X.arrow_forward
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