
VII. (12 pts) Consider the following Sn2 reaction. Br -CN DMF a. assign configuration to the...
VII. (12 pts) Consider the following Sn2 reaction. Br *CN DMF a. assign configuration to the chirality center of the substrate. b. Write the structure of the product. c. assign configuration to the chirality center of the product.
What is the product of the following SN2 reaction? NaCN Br CI Br CN CICN Br CN (b) (a) (c) (d) A
4. Consider the substitution reaction below. (4 pts.) NaSH DMF Br SH this reaction proceeds through an Snl mechanism and not an SN2 mechanism a) Explain why this reaction proceeds through an b) Explain why this reaction produces a racemic mixture of products
(a) Draw a stepwise, detailed mechanism for the following reaction. Used curved arrows to show the movement of electrons. Br CN NaCN DMF NaBr (b) Assign the configuration (Ror S) of the chiral centre in the substrate and product (c) List the bonds broken and formed in this reaction (d) Assume that this is an endothermic reaction. Draw an energy diagram for this reaction. Label the axes, reactants, products, E, and AH. Draw the structure for both transition states.
12) Identify the product for the following reaction? 2 Pts OCH, .CN Bry/FeBry ? NO OCH, осн, OCH, .CN OCH, CN .CN CN Br B) C) D) A) Br Br Br NO, NO NO2 NO, 13) Propose an efficient synthesis for the following transformations? (Multistep Synthesis) 8 P NO2 A NH2 Br 14) Write the products for the following reactions? 4 Pt OH PCC, excess CH OH CHC1 B) 2) (CH..S
10 pts Question9 Which reaction product is formed at 100°C? Br DMF Br Br IV O IV
12) Identify the product for the following reaction? 2 Pts осн, CN Bry/FeBry NO2 осн. OCH3 .CN OCH CN осн, CN CN Br B) A) D) Br Br Br NOZ NOZ NOZ NO2 13) Propose an efficient synthesis for the following transformations? (Multistep Synthesis) 8 Pt NO2 A) ♡ NH2 B)
3. Assign Rors configuration to the following molecules: - Br Br F Br -CH CH.CH H CH2CHE CH2CH CH, CH -CH, OH H -CH=CH2 H3C 7 Сн, HI CH(CH3)2 4. Label each pair of stereoisomers below as A,B,C,D a. Enantiomers b. Diastereomers c. Identical d. Meso Compounds u 5. Write the complete stepwise mechanism for this reaction. Show all electron flow with arrows and show all intermediate structures. (10 Points) BE CHO -Br (or CI) Br
1. Predict the product(s) (or no reaction) and reagent(s). (19
pts)
KN3 DMF KOMe DMF KOE -Br HMPA LDA THF NaO'Bu toluene
s/reactants of the SN2 reactions below. Be very careful of the stereochemistry if applicable. 8. Provide the products/reactants of the SX2 reactions below Please compare every two consecutive reactions. (1 pts, 0.25 pt each) Br + Na :C Hint: Na, and K are very easy to dissociate as Na' and K. + KCN CN + KBT + NaCl .. . + Na S-CHg dl. What is the type of the halide (1º, 2º, 3º)? d2. Which reactant is the nucleophile?...