I think 12 lbs would be a good guess. 6 quarts of water is 12 pounds. Tomatoes are mostly water- there will be space between the tomatoes, but they can be heaped up over the brim of the basket. A produce manager or truck farmer may have actually weighed such baskets and would know for sure; if so, I hope they will supply the definitive answer.
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As many as your basket can hold. Baskets come in different sizes.
There can be no equivalence. A pound is a measure of mass. A quart is a measure of volume. The two measure different things and, according to basic principles of dimensional analysis, conversion from one to the other is not valid. If you are not convinced, consider a quart of air. How many pounds? Next consider a quart of treacle. How many pounds?
Each gallon of liquid water weighs 8.33 pounds. When water freezes it expands slightly which means it would weigh slightly less, but this difference is negligible. This would mean, if there are 4 quarts in a gallon, that a quart of ice weighs about 2.1 pounds around...maybe just slightly less
1 US quart is 946.353mL
How many cups are there in a pint