Concept explainers
(a)
Interpretation:
To draw all the stereoisomers of (3S)-3-methylhexane when it is treated with Cl2
Concept introduction:
It is a chlorination reaction. The stereochemistry of the reaction depends mainly on whether the reaction occurs at a stereogenie center or any other atom, and whether a new stereogenic center is formed in it or not. An achiral starting material always gives either an achiral or a racemic product. But for the chiral, if a reaction does not occur at a stereogenic center, the configuration at a stereogenic center is retained in the product and if a reaction occurs at a stereogenic center, there is a mechanism to predict the stereochemistry of the product.
(b)
Interpretation:
To find out how many different fractions would be obtained from the isomers.
Concept introduction:
The stereochemistry of a reaction depends mainly on whether the reaction occurs at a stereogenie center or any other atom, and whether a new stereogenic center is formed in it or not.
An achiral starting material always gives either an achiral or a racemic product. But for the chiral, if a reaction does not occur at a stereogenic center, the configuration at a stereogenic center is retained in the product and if a reaction occurs at a stereogenic center, there is a mechanism to predict the stereochemistry of the product.
(c)
Interpretation:
To find out how many fractions of the isomers would be optically active.
Concept introduction:
The stereochemistry of a reaction depends mainly on whether the reaction occurs at a stereogenie center or any other atom, and whether a new stereogenic center is formed in it or not.
An achiral starting material always gives either an achiral or a racemic product. But for the chiral, if a reaction does not occur at a stereogenic center, the configuration at a stereogenic center is retained in the product and if a reaction occurs at a stereogenic center, there is a mechanism to predict the stereochemistry of the product.
Want to see the full answer?
Check out a sample textbook solutionChapter 15 Solutions
Organic Chemistry
- (9) How many chiral centers are present in a molecule of 1,3-dimethylcyclohexane? (C) 2 (D) 3 1 (A) O (10) What is the percent composition of a mixture of (S)-(+)-2-butanol, [a] = +13.52°, and (R)-(-)-2-butanol, [a] = -13.52°, with a specific rotation [a]D = -6.76° (A) 75%R 25%S (B) 25%R 75%S (C) 50%R 50%S 67%R 33%Sarrow_forwardGive reasons for the following :(i) Phenol is more acidic than methanol.(ii) The C—O—H bond angle in alcohols is slightly less than the tetrahedral angle (190°28′).(iii) (CH3)3C—O—CH3 on reaction with HI gives (CH3)3C—I and CH3—OH as the main products and not (CH3)3C—OH and CH3—I.arrow_forward2arrow_forward
- 4 But-2-enal, CH₂CH=CHCHO, is a pale yellow, flammable liquid with an irritating odour. (a) But-2-enal exists as two stereoisomers. Draw skeletal formulae to show the structure of the two stereoisomers of but-2-enal. (b) (i) Describe a simple chemical test that would show that but-2-enal is an aldehyde. (ii) Explain why this test gives a different result with aldehydes than it does with keton (c) But-2-enal also reacts with sodium borohydride, NaBH4. (i) Identify the organic compound formed in this reaction. (ii) State the type of chemical reaction occurring. (d) Precautions must be taken to prevent but-2-enal catching fire. Construct a balanced equation for the complete combustion of but-2-enal, C₂HO.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_forward10carrow_forward
- PGF 2a is a prostaglandin, a group of compounds that are responsible for inflammation (Section 19.6). (a) How many tetrahedral stereogenic centers does PGF 2a contain? (b) How many double bonds can exist as cis and trans isomers? (c) Considering both double bonds and tetrahedral stereogenic centers, what is the maximum number of stereoisomers that can exist for PGF20? OH HO -CH₂CH=CH(CH₂)3COOH CH=CHCH(OH)(CH₂)4CH3 PGF₂αarrow_forward5. (a) Compound A with molecular formula C7H8 is produced when benzene reacts with chloromethane in AICI3. When A is treated with acidic KMNO4 solution, compound B is formed. When A is treated with conc. HN0; in conc. H2SO4, a yellowish oil solution, C is formed. Draw the molecular structure of A, B and C and write an equation for the formation of A from benzene.arrow_forwarda) Give the chemical structure for each of the following compound: (i) 4-hydroxybenzoic acid (ii) 2-hexene (iii) chlorocyclohexane (iv) 2,5-dichloroheptane b) Prostaglandin are a group of C20 lipids and can be found in small amounts in all body tissues and fluids. (1) Put an asterisk on all the chiral carbon(s) present in the chemical structure of prostaglandin E. (II) Do you expect prostaglandin to be acidic or basic? (III) Circle the functional group that is responsible for the acidity / basicity. ali se odno HO OH HO Prostaglandin Earrow_forward
- (a) How will you convert:(i) Benzene to acetophenone (ii) Propanone to 2-Methylpropan-2-ol(b) Give reasons :(i) Electrophilic substitution in benzoic acid takes place at meta position.(ii) Carboxylic acids are higher boiling liquids than aldehydes, ketones and alcohols of comparable molecular masses.(iii) Propanal is more reactive than propanone in nucleophilic addition reactions.arrow_forwardA compound with formula C7H12O is treated with sodium borohydride in methanol to yield 2,2-dimethylcylopentanol. Write a reaction scheme showing the structures of the reactant, the reagents, and the product. Will the product be optically active? Explain.arrow_forwardThere are four dimethylcyclopropane isomers. (a) Write three-dimensional formulas for these isomers. (b) Which of the isomers are chiral? (c) If a mixture consisting of 1 mol of each of these isomers were subjected to simple gas chromatography, how many fractions would be obtained and which compounds would each fraction contain? (d) How many of these fractions would be optically active? tod o ors brie page 10 of 17arrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY