5.12 Problem Set 5 (Solutions) - Edubirdie

University:
Massachusetts Institute of Technology
Course:
5.12 | Organic Chemistry I
Academic year:

2023
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212

Pages:

8
Author:

garadh1q

Massachusetts Institute of Technology Problem Set 5, Due 4pm March 31 5.12, Spring 2005 1. Draw the products of the following reactions. Ignore stereochemistry. a. HH 1. NaNH2, NH3 2. 0 1. NaNH2, NH H- 14-2 H2SO4, HgSO4, H2O OH b HH 2 3. H₂O H- 17 → 2. a. Draw the molecular orbital diagram of ethyne. b. What is the pka of ethyne? 25 c. What is the pka of ethane? ~50 d. n-butyl lithium is a commercially available form of an alklyl anion. Draw the structure of the product of the following reaction. Lit 4. Starting from acetylene (also known as ethyne) and a ketone, design a synthesis of the following compound (Ignore stereochemistry). HO socetylove and = ↓ 5. Suggest a multi-step synthesis of 2-bromobutane from acetylene (ethyne). 6. a. Fill in the missing intermediates. Br Mg. Et₂O My Br b. Design a multistep synthesis for 3-deutero-2,2,4,4-tetramethylpentane from 2,2,4,4-tetramethylpentane. 2,2,4,4-tetramethylpentane D 3-deutero-2,2,4,4-tetramethylpentane CU Big hu HC Br Mg ether My Br D D

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