(a)
To determine: The structure of the
Interpretation: The structure of the alkyne that undergoes oxidative cleavage to give adipic acid and two equivalents of acetic acid is to be proposed.
Concept introduction: An oxidative cleavage results in formation of
Ozonolysis is the process, in which triple bonds of alkyne molecules cleave with ozone.
(b)
To determine: The structure of the alkyne that undergoes oxidative cleavage to give a triacid and propionic acid.
Interpretation: The structure of the alkyne that undergoes oxidative cleavage to give a triacid and propionic acid is to be shown.
Concept introduction: The oxidative cleavage results in the formation of
Ozonolysis is the process, in which triple bonds of alkyne molecules cleave with ozone.
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Chapter 9 Solutions
ORGANIC CHEMISTRY
- 4a. Which type of molecule is this? Label the nonpolar and polar regions of this molecule. Label the ester bonds and phosophodiester bonds. H₂C-0-C HC-0-C CH, CH,−N O CH₂ O CH3 4b. What products would you obtain if you performed an hydrolysis reaction? Draw them. O=C O=0arrow_forwardIII An alkyne reagent is shown in the following figure, write the products of the following reactions (if the reaction occurs in more than one step, write, and identify the species that are formed.) H, 2B12 CH3CH2CH2C CH KMNO, 1HC1 Lindlar Catalyst H,O, H,SO, HgSO4 H, Pd/C Catalystarrow_forwardPredict the major and minor products of the reaction. Name the products using systematic names. CH3CH=CH2+H2O−→−H+ major product: minor product: Predict the organic product of the reaction. Include all hydrogen atoms.arrow_forward
- Alkynes are prepared by double two halogens, so that they can both be removed. Complete the reaction sequence. Br₂ reactions. If starting with an alkene, first add 2 KOH (or 2 NaNH2)arrow_forwardin the electrophilic addition reactions exemplified in Scheme 1, Br2 is the a) nucleophile b) electrophile c) acid d) base e) arenearrow_forwardDraw the skeletal structure of the starting material needed for the reaction below (if a leaving group is needed, use Br). 1. NaCN -NH₂ 2. H₂ Pt organic reactantarrow_forward
- Hydroboration of Alkenes vs. Alkynes. Addition of an alkylboranes to a carbon- carbon double bond ("hydroboration") followed by oxidation is a common way to alcohols, for example, addition of dimethylborane to 2,3-dimethyl-2-butene yields 2,3-dimethyl-2-butanol. Me₂BH + Me₂C=CMe₂- →→ Me₂CH-CMe₂OH The reaction is more general as borane also adds to carbon-carbon triple bonds. obtain structures and energies for reactants and transition states for addition of dimethylborane (Me₂BH) to both ethylene and acetylene. Which reaction has the lower activation energy? Offer an explanation for your result.arrow_forwardQuestion 16arrow_forwardFree radical halogenation is used to replace one or more hydrogens on an alkane with one or more halogens (either chlorine or bromine). It is a substitution reaction. A student performs a free radical bromination on 3-methyl-pentane (5.88 g) to create the desired product of 3-bromo-3-methyl-pentane. The product mix, which hopefully contains almost all 3-bromo-3-methyl-pentane, is cleaned up by passing it through a gas chromoatograph, which separates out the 3-bromo-3-methyl-pentane from any undesired products made during the reaction (undesired products are created frequently in free radical halogenation). The initial product mix weighed 9.45 g; the purified 3-bromo-3-methyl-pentane weighed 7.21 g. What is the student's percent recovery?arrow_forward
- Diazomethane, CH2N2, is used in the organic chemistry laboratory despite its danger because it produces very high yields and is selective for reaction with carboxylic acids. Write the products of the following reactions.arrow_forwardOE 2 O NH Draw the structure of all organic products formed in the following reaction. <-5 1. KOH 2. (CH₂)₂CHCH₂Cl 3. OH, H₂Oarrow_forwardAlcohols can be converted to alkyl bromides using PBr3, which causes a complete inversion of stereochemistry. OH 10 PBr 3 Draw the stepwise mechanism for bromination of an alcohol. Be sure to include non-zero formal charges and lone pairs as necessary. : OH Br of 0 Br. Br Br Add/Remove step X Click and drag to st= drawing a structurarrow_forward
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