Interpretation:
The reason for the failure 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
Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.
Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.
Dehydration of alcohols includes the first step as the protonation of alcohol and formation of carbocation.
The order of stability of carbocation is such that the tertiary carbocation is most stable, whereas the primary carbocation is least stable and secondary carbocation lies between primary and secondary carbocation.
For naming bicyclo-compounds:
Compounds containing two fixed or bridged rings are known as bicycloalkanes.
Then number of carbon atoms in each bridge is written in square brackets in decreasing order.
For numbering substituent groups, start numbering from the longest chain, then the moderate chain, and at last, the shortest chain.
Want to see the full answer?
Check out a sample textbook solutionChapter 7 Solutions
EBK ORGANIC CHEMISTRY
- The compound below is treated with chlorine in the presence of light. CH-CH3 Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond. . You do not have to consider stereochemistry. You do not have to explicitly draw H atoms.arrow_forward(3) HI does not undergo free radical addition with 1-butene, even in the presence of a peroxide. Please provide an explanation by analyzing the propagation steps if the same radical reaction occurred with HI. Besides the bond dissociation enthalpies in the appendix, the following approximate bond dissociate enthalpies might be useful to you: ~310 kJ/mol The component of C=C CH3CH₂CH₂CH₂-Br CH3CH₂CH₂CH2-I -290 kJ/mol (C-Br bond) ~235 kJ/mol (C-I bond)arrow_forwardBromine reacts with alkenes in methanol according to the equation (see image 1). When this reaction was carried out with 4-tert-butylcyclohexene, only one isomer was formed with the molecular formula C12H23BrO (80% yield) a) Which of the following is the structure more reasonable for this compound? (see image 2) b) Explain your reasoning through a corresponding mechanismarrow_forward
- 2. Using the Roman Numerals provided, rank the following compounds in order of increasing boilıng point. Briefly explain your answer (you should justify the position of each compound in the ranking). () 2,3-dimethylheptane (I) pentane (III) 2-methylbutane (IV) 2,2-dimethylpropane Rank:arrow_forward4. Classify the following reactions as additions, eliminations, substitutions, or rearrangements: (а) CH3Br + KОН — СH3ОН + KBr (b) СH3CH2CІ + NaOH (c) H2C=CH2 + H2 → CH3CH3 H2C=CH2 + NaCl 5. Which of the following are most likely to behave as electrophiles, and which as nucleophiles? Explain. (a) NH4+ (b) C=N- (c) Br+ (d) CH3NH2 (е) Н—С—С-—нarrow_forwardThe ground rules are: you may start with anything that incorporates no more than 5 carbons in your structure per reaction with the exceptions that halobenzenes, phenol, and thiophenol are allowed and work towards this final product. (Z)-1-ethyl-2-(1-phenyl-6-propoxyhept-2-en-1- yl)disulfanearrow_forward
- II) Reactions - Complete the following reactions by drawing clear structures for the major organic product, reagent, or reactant. Remember stereochemistry (where applicable)! a) b) d) Notes on inputting answers in boxes: If the answer is a single compound, give its structure clearly. If the answer is a racemic mixture, you may give one enantiomer's structure clearly and write "racemic" or (+) under the answer. If the answer is a mixture of diastereomers, you must clearly give the individual structure of each product. . 1. NaH 2. Na, NH3 structure 1) F3C OOH 2) FeCl3, (1 equiv) H₂N. xs H₂, Pd/C 1) (sia)₂BH 2) H₂O2, NaOH H₂O 1. Cy₂BH 2. H₂O2, NaOH, H₂O FeCl3 (1 equiv)arrow_forwardThe bicyclo [3.1.0] hexane ring system, highlighted in compound 3, is found in several natural products, including sabinene, a compound partially responsible for the flavor of ground black pepper. One method for preparing this ring system involves the conversion of compound 1 to compound 2, as shown below. Draw the structure of compound 2 and provide a reasonable mechanism for its formation. Add any remaining curved arrows to complete step one of the mechanism, and modify the given drawing as needed to show the intermediate that is formed in this step.arrow_forward3) Draw the ECSF structures of (CH3)3CO (tert-butoxide ion) and CH30º (methoxide ion). Why is (tert-butoxide a PN but methoxide a GN even though both have a full O? (As it turns out, both are SBs) Redraw (CH3)3coe (ECSF) Why PN? Redraw CH30S (ECSF) Why GN?arrow_forward
- Compound X, C,4H12Br2, is optically inactive. On treatment with strong base, X gives hydrocarbon Y, C14H10: Compound Y absorbs 2 equivalents of hydrogen when reduced over a palladium catalyst to give z (C14H14) and reacts with ozone to give one product, benzoic acid (C,Hg02). Draw the structure of compound Z. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Ignore alkene stereochemistry. • If more than one structure fits the description, draw them all. • 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. ChemDoodlearrow_forwardProvide the systematic name for each of the following isomeric esters with the chemical formula C₂H1202. (Be sure to indicate double bond stereochemistry using (E)/(Z) notation. Indicate stereochemistry in rings with the terms cis or trans. It is not necessary to use italics in writing compound names.) ball & stick ✓- + labels (E)-methyl 3-methylpent-3-enoate An error has been detected in your answer. Check for typos, miscalculations etc. before submitting your answer. ball & stick + labels isopropyl-2-methylacrylate ball & stick - + labels (E)-ethyl pent-2-enoate 12arrow_forward3) When an ethylamine (CH3CH2NH2) solution of 1-methylcyclohexene is treated with bromine (Br2), the following reaction occurs: CH3 Br2 NHET + enantiokner EINH2 Br Propose a detailed mechanism to account for the products shown; include any intermediates (provide perspective diagrams (wedge/dash notation) and resonance forms where appropriate), curved arrows, formal charges, and lone pairs as need for all species involved. Hint: the Natom has a lone pair ...arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning