Concept explainers
a)
Interpretation:
- The given substituents has to be predicted.
Concept Introduction:
Electronic effect:
Electron donating groups decreases acidity by inductive effect (withdrawal of electrons through a sigma bond). Electron withdrawal increases acidity. Electron-donating substituents destabilize a base, and decrease the strength of its conjugate acid; electron-withdrawing substituents stabilize a base, which increase the strength of its conjugate base.
Rule: The strength of a base depends on the stability of its conjugate acid.
b)
Interpretation:
The given substituents to be predicted
Concept Introduction:
Electronic effect:
Electron donating groups decreases acidity by inductive effect (withdrawal of electrons through a sigma bond). Electron withdrawal increases acidity. Electron-donating substituents destabilize a base, and decrease the strength of its conjugate acid; electron-withdrawing substituents stabilize a base, which increase the strength of its conjugate base.
Rule: The strength of a base depends on the stability of its conjugate acid.
c)
Interpretation:
- The following substituents to be predicted.
Concept Introduction:
Electronic effect:
Electron donating groups decreases acidity by inductive effect (withdrawal of electrons through a sigma bond). Electron withdrawal increases acidity. Electron-donating substituents destabilize a base, and decrease the strength of its conjugate acid; electron-withdrawing substituents stabilize a base, which increase the strength of its conjugate base.
Rule: The strength of a base depends on the stability of its conjugate acid.
d)
Interpretation:
- The following substituents to be predicted.
Concept Introduction:
Electronic effect:
Electron donating groups decreases acidity by inductive effect (withdrawal of electrons through a sigma bond). Electron withdrawal increases acidity. Electron-donating substituents destabilize a base, and decrease the strength of its conjugate acid; electron-withdrawing substituents stabilize a base, which increase the strength of its conjugate base.
Rule: The strength of a base depends on the stability of its conjugate acid.
e)
Interpretation:
- The following substituents to be predicted.
Concept Introduction:
Electronic effect:
Electron donating groups decreases acidity by inductive effect (withdrawal of electrons through a sigma bond). Electron withdrawal increases acidity. Electron-donating substituents destabilize a base, and decrease the strength of its conjugate acid; electron-withdrawing substituents stabilize a base, which increase the strength of its conjugate base.
Rule: The strength of a base depends on the stability of its conjugate acid.
f)
Interpretation:
- The following substituents to be predicted.
Concept Introduction:
Electronic effect:
Electron donating groups decreases acidity by inductive effect (withdrawal of electrons through a sigma bond). Electron withdrawal increases acidity. Electron-donating substituents destabilize a base, and decrease the strength of its conjugate acid; electron-withdrawing substituents stabilize a base, which increase the strength of its conjugate base.
Rule: The strength of a base depends on the stability of its conjugate acid.
Want to see the full answer?
Check out a sample textbook solutionChapter 8 Solutions
ORGANIC CHEM ALC&STU S/G&S W/MASTER CHE
- Order the following substituents from highest priority to lowest priority: CH3, OH, H,F. Use the Cahn-Ingold-Prelog priority system. a. F, CH3, OH, H b. H, CH3, F, OH c. F, OH, CH3, H d. H, CH3, OH, Farrow_forward1 i. What is Resonance Theory? Sate five conclusions that can be drawn from the theory. ii. State the two main experiments that were used to establish the extra stability of the benzene molecule. iii. What are the factors that confer Aromaticity to an organic molecule? iv. State the effects of substituents on a benzene derivative towards further aromatic substitution. V. Based on the above suggest the various types of substituents that can be attached to Benzene.arrow_forwardFor each of the following substituents, indicate whether it withdraws electrons inductively, donates electrons by hyperconjugation, withdraws electrons by resonance, or donates electrons by resonance. (Effects should be compared with that of a hydrogen; remember that many substituents can be characterized in more than one way.) a. Br b CH2CH3 c. C=OCH3 d. NHCH3 e. OCH3 f. +N(CH3)3arrow_forward
- Show how HC≡CH, CH3CH2Br, and (CH3)2CHCH2CH2Br can be used to prepare CH3CH2C≡CCH2CH2CH(CH3)2. Show all reagents, and use curved arrows to show movement of electron pairs.arrow_forwardTRUE OR FALSE. Write T if True, F if False. 1. In numbering the longest chain, the first substituent should have the higher number. 2. Alphabetize the names of the substituents, ignoring all prefixes except iso, as in isopropyl and isobutyl. 3. A number is always designated to indicate the location of a single substituent in cyclohexane. 4. For rings with two different substituents, number the ring to assign the lower number to the substituents alphabetically. 5. In naming alkenes, the longest carbon chain is always used as the parent name. 6. Toluene is an IUPAC name. 7. A benzyl group differs from a phenyl group only by an extra CH2 group. 8. Naming of branched molecules depend on the type of C atom removed from the parent chain. 9. An unbranched alkane with a chain of 50 carbons is called pentacontane. 10. Heterocyclic amines still…arrow_forwardTRUE or FALSE. All electron-withdrawing substituents of benzene will tend to direct subsequent substituents at the 2 position in the ring.arrow_forward
- Rank the following groups in order of decreasing priority according to the Cahn-Ingold-Prelog system. I) -CH=CH2 II) -CH3 III) -CH IV) -OH 1) IV > III > I > II 2) IV > I > III > II 3) III > IV > I > II 4) II > I > III > IVarrow_forwardWhich group in each pair is assigned the higher priority in R,S nomenclature? a. – CD3, – CH3 b. – CH(CH3)2, – CHOH c. – CH2Cl, – CH2CH2CH2Br d. – CH2NH2, – NHCH3arrow_forwardThe central carbon atom of an allene is a member of two double bonds, and ithas an interesting orbital arrangement that holds the two ends of the molecule at rightangles to each other. Draw the two enantiomers of penta-2,3-diene. A model may be helpful.arrow_forward
- what aromatic annulene has the same number of bond molecular orbital as the hypothetical all cis (20) annulenearrow_forward1. Does your unknown contain any Br atoms? Cl? Odd number of N? Why or why not? 2. Give a molecular formula for your product if it contains no oxygens. Give the molecular formulas if your product contains one and two oxygens (some may not be possible). 3. Calculate the index of hydrogen deficiency, and therefore the number of rings and/or p-bonds in your unknown for each of the molecular formulas in question 3. Show your calculations.arrow_forwardGive a molecular formula for your product if it contains no oxygens. Give the molecular formulas if your product contains one and two oxygens (some may not be possible). The molecular formula for if my molecule does not have any oxygens is C6H6, if it has one oxygen it would be C7H6O, if it was two it would be C8H7O2. Calculate the index of hydrogen deficiency, and therefore the number of rings and/or p- bonds in your unknown for each of the molecular formulas in question 3. Show yourcalculationarrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning