(a)
Interpretation: The diastereomers of
Concept introduction: The addition of Halogens to
(b)
Interpretation: The diastereomers of
Concept introduction: The addition of Halogens to alkenes is a stereospecific reaction. The resultant product is meso compound, if alkene is cis and addition of halogen is syn addition. If addition of halogen is anti, then the resultant products are racemic mixture. In case of trans alkene, the resultant product is meso, if addition of halogen is anti. The resultant products are racemic mixture, if the addition of halogen is syn.
Want to see the full answer?
Check out a sample textbook solutionChapter 10 Solutions
Organic Chemistry-Package(Custom)
- The alkyl halide cis-1-bromo-4-methycyclohexane (A) undergoes a (c) substitution reaction when treated with H,0 to give a racemic mixture which is made up of product B and C. (i) What is a racemic mixture? (ii) Draw all the possible diastereoisomers of the compound below. Br Brarrow_forward(a) Draw all stereoisomers formed by monochlorination of the cis and trans isomers of 1,2-dimethylcyclobutane drawn below. (b) How many constitutional isomers are formed in each reaction? (c) Label any pairs of enantiomers formed.arrow_forwardUsing cis- and trans-hex-3-ene, demonstrate that the addition of HCl is not a stereospecic reaction. Draw the structure of the stereoisomers formed from each alkene.arrow_forward
- The structure of A is shown below. HO 3 -CH2CH=CH2 A (i) Predict the possible number of stereoisomers A can have. (ii) Draw the 3D structure of the (25, 3R, 5S) enantiomer showing its correct stereochemistry. (iii) Calculate the specific rotation of each enantiomer in a mixture containing 10 mL (0.10 M) of (2S, 3R, 55) enantiomer and 30 mL (0.10 M) of (2R, 3S, 5R) enantiomer. Given the specific rotation of the mixture = +4.8°.arrow_forwardThe reaction of (2S)-2-chloro-3-methylpentane with sodium iodide yields two products: (2R)-2-iodo-3-methylpentane and racemic 3-iodo-2-methylpentane. Account for the formation of each of these two products. For each product, you should show how it is formed and what that tells you about the mechanism of that specific reaction.arrow_forward(a) (R)-1,1,2-trimethylcyclohexane, label each structure you have drawn as chiral or achiral.arrow_forward
- Reaction of this bicycloalkene with bromine in carbon tetrachloride gives a trans dibro- mide. In both (a) and (b), the bromine atoms are trans to each other. However, only one of these products is formed. CH3 CH3 CH3 Br Br CH,Cl, + Br2 or Br Br (a) (b) Which trans dibromide is formed? How do you account for the fact that it is formed to the exclusion of the other trans dibromide?arrow_forwardIdentify the following reactions as either SN1, SN2, E1, or E2: (a) Br CHCH3 CH=CH2 КОн (b) Br OCH3 CHCH3 .CHCH3 CH3OH Нeatarrow_forward5b) Draw the expected product(s) resulting from the following SN2 reaction:arrow_forward
- 1. At what position and on what ring would you expect the following substances to undergo electrophilic substitution? (b) CH3 Br lel CH3 2. Rank the compounds in each group according to their reactivity toward electrophilic substitution. (a) Chlorobenzene, o-dichlorobenzene, benzene (b) p-Bromonitrobenzene, nitrobenzene, phenol (c) Fluorobenzene, benzaldehyde, 0-xylene (d) Benzonitrile, p-methylbenzonitrile, p-methoxybenzonitrilearrow_forwardHow many stereoisomers are generated by the reaction below? (1) Hg(OAc)2, H20/THF (2) NABH/ethanol Oa pair of enantiomers Oa single stereoisomer a pair of diastereomers four stereoisomersarrow_forwardIdentify compound Y? На + X Lindlar Pd Brz CH3– -CH3 Y 2-bromobutane meso-2,3-dibromobutane racemic (2R,3R) and (2S,3S)-2,3-dibromobutane 2,3-dibromo-2-butenearrow_forward