Concept explainers
There are two contributing resonance structures for an anion called acetaldehyde enolate, whose condensed molecular formula is
Trending nowThis is a popular solution!
Chapter 1 Solutions
Organic Chemistry
Additional Science Textbook Solutions
Organic Chemistry (8th Edition)
Chemistry: Structure and Properties (2nd Edition)
Chemistry: A Molecular Approach
Fundamentals of Heat and Mass Transfer
Living By Chemistry: First Edition Textbook
The Organic Chem Lab Survival Manual: A Student's Guide to Techniques
- The structure of Vitamin C (ascorbic acid) is shown below. As the name indicates, the molecule is somewhat acidic. Actually, one of the hydrogens on the four OH groups is much more acidic than the other three ones. Which one is the acidic hydrogen? Hints: To find the answer, you will again have to draw some resonance structures of the product formed after loss of H+. Consider the product after the loss of H+ for each of the OH groups. Only two of the OH groups have resonance structures after deprotonation; one of these two groups has a much better resonance structure than the other one (again after deprotonation). Note that the oxygen atom that is part of the five-membered ring has nothing to do with the problem.arrow_forwardSpecify whether the two structures are resonance contributors to the same resonance hybrid. Be sure to explain your reasoning. If yes, be sure to specify which is preferred and why. H2C=NH2arrow_forwardList the bond lenghts between the carbon and the oxygen atoms for the carboxylic acid and carboxylate ion and rank from shortest to longest. carboxylic acid carboxylate ion c-o c=o provide an explanation for the differences in the bond lengths and the orientation of the dipole moment between the acid and ion.arrow_forward
- Rank the following in order of decreasing importance as contributing structures to the resonance hybrid of formaldehyde, H₂CO. :0: Multiple Choice I>>||| I> ||| > | #>I> | 11 E III 200arrow_forwardMethyl isocyanate, CH3 -N= C = O, is used in the industrial synthesis of a type of pesticide and herbicide known as a carbamate. As a historical note, an industrial accident in Bhopal, India, in 1984 resulted in leakage of an unknown quantity of this chemical into the air. An estimated 200,000 people were exposed to its vapors, and over 2000 of these people died. Q.) Write a Lewis structure for methyl isocyanate and predict its bond angles. What is the hybridization of its carbonyl carbon? Of its nitrogen atom?arrow_forwardSelect the bonds in the 3D representation of methyl urethane below that are multiple bonds. (Hint: Consider the number of bonds attached to an atom in the image compared to the normal valence of that atom. In a valid structure, the number of bonds to an atom will equal the valence of that atom.) • Gray = C: white = H; red = 0; blue = N; dark green = Cl; brown = Br; light green = F; purple = 1; yellow = S: orange = P. • Double click to select bonds. You can zoom in and out using the mouse scroll wheel (or pinch to zoom on touch screens). ●arrow_forward
- Rank the following compounds in order of decreasing dipole moment. H H H H O|||||| O|||||II || 1>||| O I>II>III H ||| ||||arrow_forwardWhich of the following is a correct resonance structure for compound A? NH ΝΗ || A NH + ||| ΝΘ + IVarrow_forwardLike several other bonds, carbon-oxygen bonds have lengths and strengths that depend on the bond order. Draw Lewis structures for the following species, and arrange them in order of increasing carbon-oxygen bond strength. (Indicate the order with the numbers from the drop-down list, starting with 1 for the compound with the smallest bond strength to 5 for the compound with the largest bond strength.) H2CO CH4O CO HCO3-(H attached to O) CO32-arrow_forward
- 7 The pentadienyl radical, H2C“CH¬CH“CH¬CH2#, has its unpaired electron delocalized over three carbon atoms.(a) Use resonance forms to show which three carbon atoms bear the unpaired electron.arrow_forwardHydrogen cyanide can be catalytically reduced with hydro-gen to form methylamine. Use Lewis structures and bond ener-gies to determine ΔH°ᵣₓₙ for HCN(g)+2H₂(g)→CH₃NH₂(g)arrow_forwardWhat steps would you need to take to calculate the pKa1 and pKa2 of something? For example: hydrosulfuric acid H2S(aq) (-38.6 ΔH^0 f kJ mol^-1).arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning