Concept explainers
Phenol (shown below) has a
a. Based on
b. Draw the conjugate base of phenol (called phenoxide) including allimportant resonance structures.
c. Construct an explanation for why phenol is a stronger acid than anordinary alcohol. (You may want to consider first why phenoxide is lowerin PE than methoxide
Want to see the full answer?
Check out a sample textbook solutionChapter 5 Solutions
Custom eBook for Organic Chemistry
- Draw the most likely conjugate base resulting from this acid-base reaction. Include all lone pairs. Ignore inorganic byproducts. NaOCH2CH3 Draw Conjugate Base N aarrow_forwardWhich N atom in chloroquine is the strongest base?arrow_forwardCan you explain how you find the answer? And the steps you took? List the reasons and explain each pleasearrow_forward
- Can you explain how you find the answer? And the steps you took? Are they talking about Lewis or bronsted acid/base? How do you know?arrow_forwardhydrogens on a carbon adjacent to a carbonyl group are far more acidic than those not adjacent to a carbonyl group. The anion derived from acetone, for example, is more stable than is the anion derived from ethane. Account for the greater stability of the anion from acetone. CH,ČCH, H CH,CH, H Acetone Ethane pK, 20.2 pK, 51arrow_forwardleft 4. Consider the following equilibrium: 29925610 + Aga weak and Sung base Bast CORS + 1ght base: Strong ad d AddOH ress stable OH Is the carboxylate anion (CH3CH₂COO) an appropriate base to deprotonate the alcohol? A) yes, because the equilibrium favors the left side B) yes, because the equilibrium favors the right side C) no, because the equilibrium favors the left side D) no, because the equilibrium favors the right side OH COO basarrow_forward
- 1. Consider the following unequal equilibrium. Which two species in this equilibrium represent the weaker acid and the weaker base? CH3CH3 + CH3NH 1 2 O 1 and 4 2 and 3 1 and 2 3 and 4 ? → CH3CH₂ 3 CH3NH₂ 4arrow_forwardI know that the 3rd one (second on the right side) has the highest pka because it's an alcohol and an alcohol is less acidic than a phenol. but I don't understand which compound has the lowest pka (strongest acid)?arrow_forwardWhich of the following is the strongest base? O a. Cl-CH2CH2NH2 Ob. Cl-CH2CH2CH2NH2 O c. Cl-aromatic ring-NH2 O d. Cl-CH2 -NH2 O e. C12-aromatic ring -NH2arrow_forward
- Draw the product formed when phenylacetaldehyde (CsH;CH,CHO) is treated with each reagent. Phenylacetaldehyde is partly responsible for the fragrance of the flowers of the plumeria tree, which is native to the tropical and subtropical Americas. e. Ph;P=CHCH3 f. (CH),CHNH2, mild acid g. (CH,CH)NH, mild acid h. CH,CH,OH (еxсess), H' а. NaBHa, CH,Oн b. [1] LIAIH4; (2] H20 c. [1] CH;MgBr; [2] H2O i. NH, mild acid d. NaCN, HCI j. HOCH,CH;OH, H*arrow_forwardPhenol has a pka = 10.0. 4-Hydroxybenzaldehyde has a pka = 7.3. Draw resonance forms of the conjugate base of both and explain why 4-hydroxybenzaldehyde is more acidic. (Acidic H is underlined.) OH phenol OH -H* - H* 4-hyroxybenzaldehydearrow_forwardSelect the strongest base. NaOH CH3CH₂CH₂CH₂Li O (CH3)2NK O Na₂CO3arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning