Addition of oxygen nucleophiles: ROH add'n w/acid cat.; prep. of stable acetals 18.13) ● ● aldehydes/ketones react w/ROH to form unstable/unisolable hemiacetals aldehydes/ketones react w/2 equiv. of ROH and acid catalyst to afford stable/isolable acetals, with a hemiacetal as a mechanistic intermediate Sample rxn: Propose the mechanism: + 2 CH3 H H* (cat.) X OCH3 + (chap. 17 & 18) Note: acetal carbon has same oxid. state as C=O carbon OCH3 H an acetal (NOT an ether or "diether")

Addition of oxygen nucleophiles: ROH add'n w/acid cat.; prep. of stable acetals 18.13) ● ● aldehydes/ketones react w/ROH to form unstable/unisolable hemiacetals aldehydes/ketones react w/2 equiv. of ROH and acid catalyst to afford stable/isolable acetals, with a hemiacetal as a mechanistic intermediate Sample rxn: Propose the mechanism: + 2 CH3 H H* (cat.) X OCH3 + (chap. 17 & 18) Note: acetal carbon has same oxid. state as C=O carbon OCH3 H an acetal (NOT an ether or "diether")

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

See similar textbooks

Similar questions

(19, 5) Draw structures for the carbonyl electrophile and enolate nucleophile that react to give the aldol or enone below. You do not have to consider stereochemistry. Draw the enolate ion in its carbanion form. Draw one structure per sketcher.
(30) Br: route Please provi de complete multI Step Synthetic vapen Include Intermeda te steps (No Mechanism or transition states) include reagents
(12. 0) 2. Show by writing a suitable series of reactions, how could you prepare each of the following compounds from designated starting materials. Assume all reagents are available. Please write all reagents required and structural formulas of organic reactants and organic products for each step of your synthesis. For full marks you must write each step of your synthesis separately. Br a) from CH3-CHOH-CH,-CH3 b) CH3-CH-CH-CH3 ОН ОН frpm
9.43 Draw the organic product(s) formed when CH3CH2CH2OH is treated with each reagent. a. H2SO4 b. NaH c. HCI + ZnCl2 d. HBr e. SOCI 2, pyridine f. PBr3 g. TsCl, pyridine h. [1] NaH; [2] CH3CH2Br i. [1] TsCl, pyridine; [2] NaSH j. POCl3, pyridine
What percent of imidazole is protonated at physiological pH (7.4)?
1. For each pair of compounds, which has the polar n bond that will undergo nucleophillic additon more rapidly? Why?(17.35). (b) Less Sterre ntaderance (a) St CF3 CH3 or or (c) CI () -CEN or H,C-CEN or CL
B. Supply the missing reagent, product or starting material of the following reactions. 1. 2. 3. 4. & H 1. NaCN 2. H₂SO4, H₂O H Zn(Hg), H3O+ NH,NH), KOH OH I Reagent I:
3.32 In each of the following cases, identify whether the reagent shown is suitable to accomplish the task described. Explain why or why not: a. To protonate b. C. > Answer To protonate To protonate d. To protonate .N. using using H₂O I-Z using H₂O using H₂O
For the following questions, provide reactants, reagents, or major product(s) as required, using the principles taught in class. Assume all reagents are present in 1:1 ratios unless stated otherwise, and that no reaction is an option. 6. 7. 4. 5. OMe O₂N. of slowev nollibbs allirqosloun sri molueen jerli etsibermeni noi muinais erf wiG 8 Joi muinoin NO₂ nPrCI, AICI 3 SO3H HNO3/H₂SO4 2 equiv. W slonterov to snutounte elperilert werd CH3COCI, AICI 3 rit moitonians NO₂
1. 2. 4 CO₂CH3 1. OCH3 2. + a = Electrophilic addition b = E2 Elimination C = SN1 Nucleophilic substitution el H₂N OEt + Bu₂N OH d SN2 Nucleophilic substitution e= Electrophilic aromatic substitution f = Carbonyl nucleophilic addn CO₂Et CO₂CH3 g = Nucleophilic subs at carbonyl(acyl Xfer) h HOCH 3 = Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - i for your answers. Conjugate (nucleophilic) addn
5.66 A mixture contains equal amounts of compounds A-D. A B C a. Which compounds alone are optically active? b.If the mixture was subjected to fractional distillation, how many fractions would be obtained? c. How many of these fractions would be optically active?
17.28 Give the IUPAC name for each compound. b. CH₂CH₂ c. CH₂ d. NH₂ CI CI Br X Br NH₂ e. O₂N OH NO₂ 9. CH₂CH₂ Br c Ph CH₂CH₂CH₂ CH(CH₂)2