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Concept explainers
Interpretation:
Reason behind in the lack of optical activity in the 2- chlorobutane.
Concept introduction:
Electrophile (negative-charge loving): A molecule or ion that accepts a pair of electrons to make a new covalent bond is called an electrophile.
Electrophiles are neutral or positively charged species, having vacant orbitals and attracted electron towards itself.
Electrophilic substitution reactions: an electrophile replaces a functional group in a compound, which is typically, but not always, a hydrogen atom.
Electrophilic
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Chapter 23 Solutions
Chemistry: Atoms First (Comp. Instructor's)
- Give reasons for the following :(i) Ethyl iodide undergoes SN2 reaction faster than ethyl bromide.(ii) (±) 2-Butanol is optically inactive.(iii) C—X bond length in halobenzene is smaller than C—X bond length in CH3—X.arrow_forward(a) Draw the products of molecular formula C3H4Cl2, including stereoisomers, formed when chlorocyclopropane is heated with Cl2. (b)Assuming that compounds that have different physical properties are separable, how many fractions would be present if the mixture of products were distilled using an efficient fractional distillation? (c) How many fractions would be optically active?arrow_forwardCompound P, C4H9CI, reacts by heating with reagents KOH in ethanol to form Q (C4H8). The compound Q then undergoes acid catalysed hydration to form R (CAH100). R does not react with acidified warm sodium dichromate. (a) Determine the structure of P,Q and R (b) Give a reason why R does not react with acidified warm sodium dichromate. (c) Write chemical equation for the conversion of P to Q. (d) Draw a structural isomer of P.arrow_forward
- Give reasons :(a) n-Butyl bromide has higher boiling point than f-butyl bromide.(b) Racemic mixture is optically inactive.(c) The presence of nitro group (-NO2) at o/p positions increases the reactivity of haloarenes towards nucleophilic substitution reactions.arrow_forwardWhich of the following statements about 3-iodo-2-methylprop-1-ene is/are true? (i) It has an E isomer and a Z isomer. (ii) It can be converted to an alkyl lithium compound in one step by reacting with lithium metal. (iii) It would react with the following reagent to give 2-methylhept-1-ene as the product: CuLiarrow_forwardBiphenyl has the following structure.(a) Is biphenyl a (fused) polynuclear aromatic hydrocarbon?(b) How many pi electrons are there in the two aromatic rings of biphenyl? How does this number compare with that for naphthalene?(c) The heat of hydrogenation for biphenyl is about 418 kJ>mol (100 kcal>mol). Calculate theresonance energy of biphenyl.(d) Compare the resonance energy of biphenyl with that of naphthalene and with that of two benzene rings. Explain thedifference in the resonance energies of naphthalene and biphenyl.arrow_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_forwardStarting from bromoethane, the formation of which of the following compound requires more than one step of reaction? 2 (a) Methoxyethane (b) Ethanol (c) Ethanoic acid (d) Ethenearrow_forward12. Natural (2)-menthol, the essential oil primarily responsible for the flavor and aroma of peppermint, is the IR,25,5R-stereoisomer. (a) Identify (2)-menthol from the structures you drew for Problem 50, part (b). (b) Another of the naturally occurring diastereomers of menthol is (1)-isomenthol, the 1S 2R5R- stereoisomer. Identify (1)-isomenthol among your structures. (c) A third is (1)-neomenthol, the 15.25,SR-compound. Find (1)-neomenthol among your structures. (d) Based on your understanding of the conformations of substituted cyclohexanes (Section 4-4), what is the stability order (from most stable to least) for the three diastereomers, menthol, isomenthol, and neomenthol?arrow_forward
- Compound A has the molecular formula C14H25Br and was obtained by reaction of sodium acetylide (HC≡CNa) )with 1,12-dibromododecane. On treatment of compound A with sodium amide, it was converted to compound B (C14H24). Ozonolysis of compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation of compound B over Lindlar palladium gave compound C (C14H26), while hydrogenation over platinum gave compound D (C14H28). Sodium-ammonia reduction of compound B gave compound E (C14H26). Both C and E yielded O═CH(CH2)12CH═O on ozonolysis. Assign structures to compound A through E so as to be consistent with the observed transformations.arrow_forwardAcid-catalyzed dehydration of 2,2-dimethyl-1-hexanol gave a number of isomeric alkenes including 2-methyl-2-heptene as shown in the following equation.(a) Write a stepwise mechanism for the formation of 2-methyl-2-heptene, using curved arrows to show the flow of electrons. (b) What other alkenes do you think are formed in this reaction?arrow_forwardGive the structures of the substitution products expected when 1-bromohexane reacts with(a) NaOCH2CH3 (b) KCN (c) NaOHarrow_forward
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- 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
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