Concept explainers
(a)
Interpretation:
Whether the peroxide is present or not, the structure of a six-carbon
Concept introduction:
The addition of one or more than one halogen atom in an
(b)
Interpretation:
The structure of four compounds of formula
Concept introduction:
The addition of
(c)
Interpretation:
The structure of two alkenes that give
Concept introduction:
The oxymercuration reaction is an electrophilic addition reaction that converts an alkene into an alcohol and an
(d)
Interpretation:
The structure of an alkene with one double bond that would give only one product after ozonolysis followed by hydrogen peroxide is to be stated.
Concept introduction:
In oxidative cleavage both the sigma and pi bond of the alkene is broken and two carbonyl compounds are formed. When ozone is added to the alkene, unstable intermediate molozonide is formed which rearranges to ozonide.
(e)
Interpretation:
The structure of two stereoisomeric alkenes that would give
Concept introduction:
Hydroboration reaction is a two step reaction, which involves conversion of alkene into alcohol. This type of reaction follows anti-Markovnikov rule.
Anti markovinkov rule states that the positive part of acid attached to that carbon atom in
(f)
Interpretation:
The structure of an alkene with five carbons that would give the same product as a result of either oxymercuration-reduction or hydroboration-oxidation is to be drawn.
Concept introduction:
Hydroboration reaction is a two step reaction, which involves conversion of alkene into alcohol. This type of reaction follows anti-Markovnikov rule.
Anti markovinkov rule states that the positive part of acid attached to that carbon atom in
Want to see the full answer?
Check out a sample textbook solutionChapter 5 Solutions
Organic Chemistry
- 1. 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(a) A hydrocarbon isolated from fish oil and from plankton was identified as 2,6,10,14-tetramethyl-2-pentadecene. Write its structure.(b) Alkyl isothiocyanates are compounds of the type RN C S. Write a structural formula for allyl isothiocyanate, a pungent-smelling compound isolated from mustard.(c) Grandisol is one component of the sex attractant of the boll weevil. Write a structural formula for grandisol given that R in the structure shown is an isopropenyl group.arrow_forward2-bromo-2-methylbutane undergoes hydrolysis reaction with water, H2O toform compound W. Compound X and compound Y are produced when 2-bromo-2-methylbutane undergoes elimination reaction with alcoholic ofsodium hydroxide, NaOH. (i) Draw the structural formula of compounds W, X and Yarrow_forward
- (a) Give an acceptable name for compound A. (b) Draw the organic products formed when A is treated with each reagent: [1] H3O+; [2] −OH, H2O; [3] CH3CH2CH2MgBr (excess), then H2O; [4] LiAlH4, then H2O.arrow_forwardCompound X (C4H9Br) reacts by heating with NaOH in H2O to form Y. The compound Y then undergoes acid catalysed hydration by H2SO4 in 180°C to form 2-methyl prop-1-ene. (e) Determine the structure of X and Y. (f) Predict a MAJOR product when compound Y reacts with H2SO4 in 140°C. (g) Draw a structural isomer of X. Name the isomer using IUPAC nomenclature. (h) Describe a chemical test to distinguish between compound Y and 1-butanol.arrow_forward(a) rate at which the following alcohols undergo dehydration to form alkenes in sulfuric acid OH OH OH (b) rate at which the following alkenes undergo addition with HBr to form an alkyl halidearrow_forward
- 10. Compound X (C4H9Br) reacts by heating with NaOH in H2O to form Y. The compound Y then undergoes acid catalysed hydration by H2SO, in 180°C to form 2-methyl prop-1-ene. (e) Determine the structure of X and Y. (f) Predict a MAJOR product when compound Y reacts with H2SO4 in 140 C. (g) Draw a structural isomer of X. Name the isomer using IUPAC nomenclature. (h) Describe a chemical test to distinguish between compound Y and 1-butanol.arrow_forwardArrange the alkenes in each set in order of increasing rate of reaction with HI and explain the basis for your ranking. Draw the structural formula of the major product formed in each case. (a) and (b) H3CH₂CHC=CH₂ and (H3C) 2C=CHCH3arrow_forwardName the following aldehydes and ketones: (a) (b) CH2CH2CHO CH3CH2CCHCH3 CH3 Draw structures corresponding to the following names: (b) 4-Chloropentan-2-one (e) 3-Methylbut-3-enalarrow_forward
- Deduce the structure of each compound from the information given. All unknowns in this problem have molecularformula 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 dimethylsulfide, gives two equivalents of butanedial, O“CH¬CH2CH2¬CH“O. Draw the structure of X.(c) Upon catalytic hydrogenation, unknown Y gives cyclooctane. Ozonolysis of Y, followed by reduction with dimethylsulfide, gives a three-carbon dialdehyde and a five-carbon dialdehyde. Draw the structure of Y.*(d) Upon catalytic hydrogenation, unknown Z gives cis-bicyclo[4.2.0]octane. Ozonolysis of Z, followed by reductionwith dimethyl sulfide, gives a cyclobutane with a three-carbon aldehyde (¬CH2¬CH2¬CHO) group on C1 and aone-carbon aldehyde (¬CHO) group on C2. Draw the…arrow_forwardGive the structures of the products you would expect when each alcohol reacts with(1) HCl, ZnCl2; (2) HBr; (3) PBr3; (4) P>I2; and (5) SOCl2.(a) butan-1-ol (b) 2-methylbutan-2-ol(c) 2,2-dimethylbutan-1-ol (d) cis-3-methylcyclopentanolarrow_forwardPredict the major products (including stereochemistry) when cis-3-methylcyclohexanol reacts with the following reagents. (a) concentrated HBr (b) TsCl/pyridine, then NaBrarrow_forward