Complete the following Grignard reaction. The starting material is chiral and present as a single enantiomer. Using models, predict which product enantiomer predominates and include that stereochemical prediction in your answer. `MgBr 1. 2. Н.О, НС Ha H.
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- Provide products for the following reactions. Label them as chiral, achiral, meso, dl, cis/trans, and stereocenters as R,S.Which of these products is the result of a hydride shift occuring during the substitution reaction of aqueous 2-chloro-3-methylpentane? CH3CH2CCH2CH3 || CH2 CH3CH(OH)CH(CH3)CH2CH3 CH2=CHC(CH3)=CHCH3 CH3CH=C(CH3)CH2CH3 CH3CH2C(CH3)CH2CH3 | OHA difficult problem in the synthesis of PGF2α is the introduction of the OH group at C15 in the desired configuration. a. Label this stereogenic center as R or S. b. A well known synthesis of PGF2α involves reaction of A with Zn(BH4)2, a metal hydride reagent similar in reactivity to NaBH4, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship. c. Suggest a reagent to convert A to the single stereoisomer X.
- 4. The following molecule was subjected to two different conditions. Provide the product in each case. 1. Mel, K₂CO3 2. Ag₂O, A mCPBA, ΔThe transition state of a reaction is given below. Provide structures for the organic reactant and the product for the reaction. Identify the stereochemical features of both the reactant and the product (on the basis of the transition state) 4. The following pK, values may be helpful in guiding you to the correct answer: pK, HI = -9.5; pK, HCN = 9.2 CH,CH,CH(CH3)2 I------ ----CN H3C H.5. Provide the structures as necessary to complete the following sequences of reactions. Indicate stereochemistry when needed and if more than one stereoisomer can be formed just draw one of the stereoisomers unless otherwise indicated. Only organic products need to be provided. a) (excess) 1) 03 2) H202 b) Pd/C CO,Me H2 c) 1. NaH H2 2. Pd/Baso4 quinoline Br
- 4. Study the reactions listed below and decide whether the products are going to be a mixture of enantiomers, diastereomers, or neither. i. ii. iii. iv. V. Reaction Cl₂₁₂ H₂ CC14 Pt H₂O* Br₂ H₂O CCL4, hv NBS HBr Products & Mixture DiastereomersWith your models, construct a pair of enantiomers. From each of the models, remove the same common element (e.g., the white component) and the connecting links (bonds). Reconnect the two central carbons by a bond. What you have constructed is the meso form of a molecule, such as meso-tartaric acid. How many chiral carbons are there in this compound (5a)? НООС — С,Н—Сън— СООН OH OH Tartaric acid Is there a plane of symmetry (5b)? Is the molecule chiral or achiral (5c)?Please explain properly. Q16. Ibuprofen, an example of an NSAID, is the active ingredient in several popular over-the-counter analgesics in the U.S., and it is sold in racemic form, even though only the S-enantiomer is pharmacologically active. Suggest methods that might be used to obtain or prepare ibuprofen in enantiomerically pure form, based on processes and reactions you learned. H CH3 (CH3)2CHCH₂ S-ibuprofen CO₂H
- A difficult problem in the synthesis of PGF2α is the introduction of the OH group at C15 in the desired configuration. a. Label this stereogenic center as R or S. b. A well-known synthesis of PGF2α involves reaction of A with Zn(BH4)2, a metal hydride reagent similar in reactivity to NaBH4, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship. d. Suggest a reagent to convert A to the single stereoisomer X.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°.The alkene shown undergoes bromination. H (a) Draw the product(s) of bromination of this compound, including all expected stereoisomers (if any). Use wedge-and-dash bonds to designate the stereochemistry at any chirality centers, and make sure to draw an explicit hydrogen if a chirality center has one. (b) Characterize the starting alkene as having the E or Z configuration. (c) characterize the product(s). (a) H Br₂ Draw the product(s) of bromination. Br H Br