Concept explainers
(a)
To determine: The complete Lewis structure for sodium triacetoxyborohydride.
Interpretation: The complete Lewis structure for sodium triacetoxyborohydride is to be drawn.
Concept introduction: The Lewis structure shows the connectivity between atoms by identifying the lone pairs of electrons in a compound. Lewis structures are also called Lewis dot structures. The valence electrons around an atom are shown by dots. Bonds between atoms are shown by lines and the lone pair of electrons is shown by a pair of dots.
(b)
To determine: The mechanism for the reduction of an aldehyde by sodium triacetoxyborohydride.
Interpretation: The mechanism for the reduction of an aldehyde by sodium triacetoxyborohydride is to be proposed.
Concept introduction: Sodium triacetoxyborohydride is a mild reducing agent that reduces
Want to see the full answer?
Check out a sample textbook solutionChapter 18 Solutions
Organic Chemistry (9th Edition)
- 1. Propose a mechanism to account for the formation of 2,3-dimethyl-2-butene from 3,3-dimethyl-2-butanol b. Propose a mechanism to account for the formation of 1,2-dimethylcyclohexene fromthe acid-catalyzed dehydration of 2,2-dimethylcyclohexanolarrow_forwardStarting with an alkyl halide, how could the following compounds be prepared? a. 2-methoxybutane b. 1-methoxybutane c. butylmethylaminearrow_forwardWhat is the best choice of reagents to achieve the following reaction? A. SOCl2 (1/2 equivalent) B. KOH (pellets) C. K2SO4 D. PhCO2Naarrow_forward
- Reaction of HBr with 2-methylpropene yields 2-bromo-2-methylpropane. What is the structure of the carbocation formed during the reaction? Show the mechanism of the reaction.arrow_forwardReaction of hbr with 2-methylpropene yields 2 bromo 2 methylpropane. What is the structure of the carbocation formed during the reaction? Show the mechanism of reaction.arrow_forwardIn the experiment where an Electrophillic aromatic substitution sulfonation reaction is conducted on Indigo to produce the food dye FD&C Blue #2(indigo blue or indigotine). show a mechanism showing a single sulfonation on a molecule of indigo.arrow_forward
- Tunicates are marine animals that are called "sea squirts" because when they are taken out of water, they tend to contract and expel seawater. Lepadiformine is a cytotoxic agent (toxic to cells) isolated from a marine tunicate. During a recent synthesis of lepadiformine, the investigators observed the formation of an interesting by-product (3) while treating diol 1 with a reagent similar in function to PBr3 (J. Org. Chem. 2012, 77, 3390–3400):arrow_forwardWhat is the rate law implied by the mechanism given below? CH3COCH3(aq) + H+(aq) ←→ CH3C(OH)CH3+(aq) (fast, reversible) CH3C(OH)CH3+(aq) → CH3C(OH)=CH2(aq) + H+(aq) (slow) CH3C(OH)=CH2(aq) + Br2(aq) → CH3C(OH)CH2Br+(aq) + Br-(aq) (fast) CH3C(OH)CH2Br+(aq) → CH3COCH2Br(aq) + H+(aq) (fast) A. Rate = k[CH3COCH3][H+] B. Rate = k[CH3COCH3] C. Rate = k[CH3COCH3][Br2] D. Rate = k[CH3COCH3]2 E. Rate = k[CH3COCH3][Br2]/[H+] (Answer is A, looking for explanation why!).arrow_forwardThe Baylis–Hillman reaction is a DABCO (1,4-diazabicyclo[2.2.2]octane) catalyzed reaction of an a,b-unsaturated carbonyl compound with an aldehyde to form an allylic alcohol. Propose a mechanism for the reaction. (Hint: DABCO serves as both a nucleophile and as a base in the reaction.)arrow_forward
- What is a possible formula for a carbocation with m/z=97arrow_forwardChoose the best reagents from the list provided below for carrying out the following conversion. Match the reagent with the step number. HCl (aq), Zn(Hg) KMnO4, H3O+ CH3Cl, AlCl3 HNO3, H2SO4 Cl2, FeCl3 fuming sulfuric acidarrow_forwardhelp me draw the products when ethyl isopropyl ether is treated with the following reagent: 1.HBr (2 equivalents) 2.HI (in excess)arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning