use iso-, tert-, sec- prefixes in your substituent names, where necessary

Transcription

1 Chapter 07.2: 1 1) Name. Include E/Z stereochemistry in name, if necessary. a) 3 C b) c) d) e) f) use iso-, tert-, sec- prefixes in your substituent names, where necessary g) Do NT use iso-, tert-, sec- prefixes in your substituent names; instead, use IUPAC numbering to identify substituent names, where necessary

2 Chapter ) Assign E or Z configuration. CIRCLE the highest priority groups for credit. C 3 3 C C C 3 3 C C N 3 C C C C 3 N 2 N C 3 N 3 C N 3 C C C 3 C 3 C C C 3 3) Match the appropriate letter to the substituent below a. Allyl b. Phenyl c. Vinyl d. Methylene 4) assify each as (M)onosubstituted, (D)isubstituted, (TRI)substituted, or (TET)rasubstituted. Write M, D, TRI, or TET in boxes below.

3 Chapter ) Draw. a) 3-n-butyl-2-heptene b) trans-2,2,5,5-tetramethyl-3-hexene c) 3-isopropyl-2,4-dimethyl-2-pentene d) 4-ethyl-2-methyl-2-hexene 6) Arrange the following in order of increasing stability (1 is LEAST stable; 3 is MST stable). a) b)

4 Chapter 07.2: 4 7) Place a dot ( ) (this size) on top of EAC beta-carbon and draw the letter (α) next to the alpha-carbon in the alkyl halide and carbocation compounds below. Ts 8) For the E1 reactions below, 1. Provide the carbocation intermediate, then 2. Show the MST stable product Intermediate Product Intermediate Product

5 Chapter 07.2: 5 9) Arrange the following in order of increasing E2 reactivity (1 is LEAST reactive; 3 is MST reactive). c) d) 10) Consider the following data in the Table (this will not be provided on the exam, it's included here to help you understand how to approach the problems). Look at the SIZE of the base used and notice the product distribution between the Zaitsev and ofmann products. NTE: K is written as t-buk Bulkier bases typically yield proportion as the ofmann product. The smaller bases (such as Et often seen as NaEt or yields more substituted alkene as the product. 11) Identify the products of the following E2 reactions. If only a product is made, draw an X in the box. Disregard trans/cis stereochemistry as / for this problem. NaEt t-buk

6 Chapter 07.2: 6 I Na I t-buk Na t-buk NaEt NaEt NaEt

7 Chapter 07.2: 7 NaEt t-buk t-buk 12) Identify the STEREISMERIC products of the following E2 reactions NaEt NaEt

8 Chapter 07.2: 8 NaEt NaEt NaEt NaEt NaEt NaEt

9 Chapter 07.2: 9 13) Which base is used to yield the following as the product. A. t-buk B. Na Place Letter in the box. 14) Identify the STEREISMERIC products of the following E1 reactions. Notice the strong acid reactant ( 2 S 4 and ) used with an alcohol ; notice that no strong acid is used with non-alcohol in E1 reactions) 2 S 4 2 S 4 Et 2 S 4

10 Chapter 07.2: 10 2 S 4 15) Provide the reactions conditions needed 2 S 4 / R Et/ to carry out the following E1 reactions. Ts

11 Chapter 07.2: 11 16) If the following E1 reaction involves a carbocation rearrangement, draw the initial carbocation formed, the carbocation made AFTER rearrangement, and then the alkene. If no rearrangement occurs, Draw an X in the boxes. Initial Carbocation Formed Rearranged Carbocation E1 product 2 If N rearrangment, Draw X in the box Initial Carbocation Formed Rearranged Carbocation E1 product 2 S 4 If N rearrangment, Draw X in the box Initial Carbocation Formed Rearranged Carbocation E1 product 2 S 4 If N rearrangment, Draw X in the box Initial Carbocation Formed Rearranged Carbocation E1 product 2 S 4 If N rearrangment, Draw X in the box

12 Chapter 07.2: Initial Carbocation Formed Rearranged Carbocation 12 E1 product 2 If N rearrangment, Draw X in the box 17) Complete the mechanisms. Use curved arrows ( ) to show movement of bond (electrons). Cation S S Carbocation Rearrangement? If N Rearrangement draw X in Box + Loss of Use curved arrows to show mechanism of deprotonation Carbocation If N Carbocation Rearrangement, Use curved arrows to show mechanism of deprotonation Alkene + 3 +

13 Chapter 07.2: 13 Cation S S Carbocation Rearrangement? YES, Draw it; N Draw X in Box + Loss of Use curved arrows to show mechanism of deprotonation Carbocation If N Carbocation Rearrangement, Use curved arrows to show mechanism of deprotonation Alkene + 3 +

14 Chapter 07.2: 14 18) Draw the elimination product(s) for the reaction below (Include stereochemistry in products, when necessary). Ph = Phenyl Ph C 3 Ph E2 If 2 or fewer products place an X in the box(es) that you do not use 2 E1 If 2 or fewer products place an X in the box(es) that you do not use

15 Chapter 07.2: 15 19) Draw the structure of the major organic ELIMINATIN product K (K) 20) Draw the structure of the major organic ELIMINATIN product K (K) 21) Predict the alkene of the E1 reaction. E1

16 Chapter 07.2: 16 Become familiar with the reagents in the table below, this will not be provided on the exam. Find trends, make up mnemonics that help you remember those trends, if necessary. (Na) (NaS) (Na) (Na) (NaI) (NaSR) (NaMe) (NaEt) (t-buk) (Bulky base) S N 2 or S N 1 reagents E2 conditions E2/S N 2 conditions E1/S N 1 conditions DBN: strong base, weak nucleophile DBU: strong base, weak nucleophile 22) The mechanism(s) for the reaction below is: (CIRCLE mechanism(s) below) Na E1 S N 1 E2 S N 2 23) The mechanism(s) for the reaction below is: (CIRCLE mechanism(s) below) DBN E1 S N 1 E2 S N 2 24) The mechanism(s) for the reaction below is: (CIRCLE mechanism(s) below) NaI in DMS what type of solvent is DMS? E1 S N 1 E2 S N 2

17 Chapter 07.2: 17 25) The mechanism(s) for the reaction below is: (CIRCLE mechanism(s) below) t-buk E1 S N 1 E2 S N 2 26) The mechanism(s) for the reaction below is: (CIRCLE mechanism(s) below) t-buk E1 S N 1 E2 S N 2 27) The mechanism(s) for the reaction below is: (CIRCLE mechanism(s) below) Et E1 S N 1 E2 S N 2

18 Chapter 07.2: 18 28) Consider the reactions below for questions I I acetone I acetone I acetone 29) The alkyl bromide starting materials in these reactions are classified as A) 3 B) 4 C) 1 D) 2? LETTER here 30) The solvent (acetone) in these reactions is: A) polar protic B) nonpolar protic C) nonpolar aprotic D) polar aprotic LETTER here 31) Circle the faster reaction above? 32) The mechanism for both reactions above is: A) E1 B) S N 1 C) E2 D) S N 2 LETTER here

19 Chapter 07.2: 19 For Reference nly (not supplied on exam) 33) Identify the product of the following reactions. SW STERECEMISTRY WEN NECESSARY Ts Na DMS t-buk Na Et

20 Chapter 07.2: 20 Na Ts DBN NaMe