Concept explainers
Interpretation:
The nucleophilic substitution reaction of
Concept introduction:
Electrophiles are electron-deficient species, which has positive or partially positive charge. Lewis acids are electrophiles, which accept electron pair.
Nucleophiles are electron-rich species, which has negative or partially negative charge. Lewis bases are nucleophiles, which donate electron pair.
Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.
Nucleophilic substitution reaction is a reaction in which an electron rich nucleophile attacks the positive or partial positive charge of an atom or a group of atoms to replace a leaving group.
The
The
In double bond or cyclic compounds, if two same
If the two functional groups are present on the different sides of the double bond or cyclic compound, the given compound can be labeled as Trans.
Cis-trans isomerism exists in the compounds in which similar groups are present on the adjacent carbon atoms.
Chair conformations: It is the most stable conformation, which accurately shows the spatial arrangement of atoms.
Equatorial bonds are parallel to the average plane of the ring, while axial bonds are perpendicular to the average plane of the ring.
The conformation having bonds at the equatorial positions are more stable than those with bonds at the axial position.
On flipping the cyclohexane ring, axial bonds become equatorial bonds and equatorial bonds becomes axial bond.
Bulkier group acquires equatorial positions to form stable conformer due to steric factors.
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Chapter 6 Solutions
ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
- 6.20 Account for the regioselectivity and stereoselectivity observed when 1-methylcyclopentene is treated with each reagent. (a) BH, (b) Br₂ in H₂O (c) Hg(OAc), in H₂O 6.21 Draw a structural formula for an alkene with the indicated molecular formula that ion product (more than one alkene may give thearrow_forward• PRACTICE PROBLEM 8.12 Treating a hindered alkene such as 2-methyl-2-butene with BH3:THE leads to the for- mation of a dialkylborane instead of a trialkylborane. When 2 mol of 2-methyl-2-butene is added to 1 mol of BH3, the product formed is bis(3-methyl-2-butyl)borane, nicknamed in reagent "disiamylborane." Write its structure. Bis(3-methyl-2-butyl)borane is a useful certain syntheses that require a sterically hindered borane. (The name “disiamyl" comes from "disecondary-iso-amyl," a completely unsystematic and unacceptable name. The name "amyl" is an old common name for a five-carbon alkyl group.) donbyarrow_forwardPRACTICE PROBLEM 8.20 Specify the alkene and reagents needed to synthesize each of the following diols. OH HO- (a) (b) (c) HO. н он HO (racemic) (racemic)arrow_forward
- O PRACTICE PROBLEM 8.14 Starting with any needed alkene (or cycloalkene) and assuming you have deuterioace- tic acid (CH3CO,D) available, outline syntheses of the following deuterium-labeled compounds.s el en olad lo nohibbs ad CH3 (a) (CH3)2CHCH2CH,D (b) (CH3),CHCHDCH3 (c) (+ enantiomer) (d) Assuming you also have available BD3:THF and CH3CO2T, can you suggest a synthesis of the following? hab erl (+ enantiomer)he imo (nwond-ben) CH3 H. (asoholea)arrow_forward6.26 There is an overall 29-fold difference in reactivity of 1-chlorohexane, 2-chlorohexane, and 3-chlorohexane toward potassium iodide in acetone. (a) Which one is the most reactive? Why? (b) Two of the isomers differ by only a factor of 2 in reactivity. Which two are these? Which one is the more reactive? Why?arrow_forwardAnswer ALL parts. (a) Draw BOTH chair conformations of trans-1,2-dichlorocyclohexane, and explain which is more stable. (b) Draw Newman projections for both the highest and lowest energy conformations of the product obtained from the reaction of (E)-but-2-ene with bromine in water.arrow_forward
- • PRACTICE PROBLEM 8.13 Specify the appropriate alkene and reagents for synthesis of each of the following alcohols by hydroboration–oxidation. (a) (c) OH (e) CH3 OH AH OH no mobe OH ( (b) (d) (f) OH HT H3 D OH OH HO OHarrow_forwardStarting with (S)-2-bromobutane, outline syntheses of each of the following compounds:• PRACTICE PROBLEM 6.19 (a) (R)-CH,CHCH,CH3 (c) (R)-CH,CHCH,CH3 OH bA-(2) ÓCH,CH3 SH muinolue for (b) (R)-CH,CHCH,CH3 (d) (R)-CH,CHCH,CH3 tho betallgo ÓCCH3 ŚCH3arrow_forward6.2 (-)-Cameroonanol has been isolated from the essential oil of Echinops giganteus (globe thistle) plants and it is associated with a strong woody fragrance. Its structure, includ- ing relative stereochemistry, was confirmed when it was made in the laboratory according to the sequence shown below.' Recall that a C=C bond is made up of one o bond and one 7 bond. These two bonds together have a combined BDE (bond dissociation energy) of 607 kJ/mol. Use this information to estimate the AH° for the conversion of compound 1 into compound 2. Br two steps H.. H HBr hv H (-Cameroonanolarrow_forward
- 5. Consider the following reaction: H-I (ii) (i) intermediate product (a) Use curved arrows to indicate the electron flow in step (i). (b) Provide the line structure of the carbocation intermediate that forms in the reaction above (c) Use curved arrows to show the electron flow in step (ii). (d) Explain briefly why the reaction in (ii) is regioselective.arrow_forwardCompounds X and Y are both C5H11CI products formed in the radical chlorination of pentane. Base-promoted E2 elimination of X and Y gives, in each case, a single C5H10 alkene (ignoring double bond stereochemistry). Both X and Y react in SN2 fashion with sodium iodide in acetone; Y reacts faster than X. What is the structure of Y? • Do not use stereobonds in your answer. • In cases where there is more than one possible structure for each molecule, just give one for each. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. ChemDoodle (Previous Nextarrow_forwardphase, allowing the simultaneous • Only reaction B is feasible because frontier orbitals of reactants can overlap in- phase, allowing the simultaneous formation of two o bonds. 6. The name of the most stable conformation of 1,3-butadiene isarrow_forward
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